# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2023
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
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data_v26
_audit_block_doi 10.5517/ccdc.csd.cc2gr9r9
_database_code_depnum_ccdc_archive 'CCDC 2286521'
loop_
_citation_id
_citation_doi
_citation_year
1 10.26434/chemrxiv-2023-78z7p 2023
loop_
_audit_author_name
_audit_author_address
'Iryna Sadkova'
;Enamine Ltd
Ukraine
;
_audit_update_record
;
2023-08-03 deposited with the CCDC. 2023-10-27 downloaded from the CCDC.
;
_audit_creation_date 2022-08-19
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number 2016/6
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C13 H13 F O2'
_chemical_formula_sum 'C13 H13 F O2'
_chemical_formula_weight 220.23
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system monoclinic
_space_group_IT_number 14
_space_group_name_H-M_alt 'P 1 21/n 1'
_space_group_name_Hall '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
_cell_length_a 12.625(3)
_cell_length_b 6.2763(14)
_cell_length_c 14.050(3)
_cell_angle_alpha 90
_cell_angle_beta 95.590(14)
_cell_angle_gamma 90
_cell_volume 1108.0(4)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 2379
_cell_measurement_temperature 273.15
_cell_measurement_theta_max 20.66
_cell_measurement_theta_min 2.91
_shelx_estimated_absorpt_T_max 0.990
_shelx_estimated_absorpt_T_min 0.980
_exptl_absorpt_coefficient_mu 0.099
_exptl_absorpt_correction_T_max ?
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_type none
_exptl_absorpt_process_details ?
_exptl_absorpt_special_details ?
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.320
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 464
_exptl_crystal_size_max 0.21
_exptl_crystal_size_mid 0.12
_exptl_crystal_size_min 0.1
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0520
_diffrn_reflns_av_unetI/netI 0.0351
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max 15
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_k_max 7
_diffrn_reflns_limit_k_min -7
_diffrn_reflns_limit_l_max 16
_diffrn_reflns_limit_l_min -16
_diffrn_reflns_number 13942
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full 24.996
_diffrn_reflns_theta_max 24.996
_diffrn_reflns_theta_min 2.071
_diffrn_ambient_temperature 273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type 'Bruker APEX-II CCD'
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source ?
_diffrn_source_current 30.0
_diffrn_source_power 1.2
_diffrn_source_voltage 40.0
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 1370
_reflns_number_total 1955
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement ?
_computing_data_collection ?
_computing_data_reduction ?
_computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement 'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max 0.159
_refine_diff_density_min -0.177
_refine_diff_density_rms 0.039
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.023
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 146
_refine_ls_number_reflns 1955
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0744
_refine_ls_R_factor_gt 0.0474
_refine_ls_restrained_S_all 1.023
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0547P)^2^+0.3550P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1097
_refine_ls_wR_factor_ref 0.1263
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups
At 1.5 times of:
All O(H) groups
2.a Ternary CH refined with riding coordinates:
C4(H4)
2.b Secondary CH2 refined with riding coordinates:
C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
C9(H9), C10(H10), C11(H11), C12(H12), C13(H13)
2.d Idealised tetrahedral OH refined as rotating group:
O1(H1)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary dual
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.29331(10) 0.01109(19) 0.51394(9) 0.0601(4) Uani 1 1 d . . . . .
O1 O 0.43683(13) 0.2630(3) 0.47120(14) 0.0781(6) Uani 1 1 d . . . . .
H1 H 0.486252 0.344599 0.464326 0.117 Uiso 1 1 calc R U . . .
O2 O 0.39495(12) 0.5190(3) 0.56918(12) 0.0684(5) Uani 1 1 d . . . . .
C1 C 0.28411(16) 0.2129(3) 0.55449(14) 0.0450(5) Uani 1 1 d . . . . .
C2 C 0.17497(15) 0.3089(3) 0.51898(13) 0.0420(5) Uani 1 1 d . . . . .
C3 C 0.10149(17) 0.1610(4) 0.57301(15) 0.0571(6) Uani 1 1 d . . . . .
H3A H 0.026014 0.191104 0.560999 0.069 Uiso 1 1 calc R U . . .
H3B H 0.116407 0.009915 0.568327 0.069 Uiso 1 1 calc R U . . .
C4 C 0.15756(18) 0.2717(4) 0.66169(15) 0.0619(7) Uani 1 1 d . . . . .
H4 H 0.123531 0.275088 0.721455 0.074 Uiso 1 1 calc R U . . .
C5 C 0.27191(18) 0.1931(4) 0.66200(15) 0.0619(7) Uani 1 1 d . . . . .
H5A H 0.279788 0.047039 0.684126 0.074 Uiso 1 1 calc R U . . .
H5B H 0.321705 0.283737 0.700171 0.074 Uiso 1 1 calc R U . . .
C6 C 0.15836(18) 0.4725(4) 0.59945(15) 0.0559(6) Uani 1 1 d . . . . .
H6A H 0.218028 0.567447 0.615633 0.067 Uiso 1 1 calc R U . . .
H6B H 0.091325 0.548977 0.591360 0.067 Uiso 1 1 calc R U . . .
C7 C 0.37960(15) 0.3400(3) 0.52942(14) 0.0450(5) Uani 1 1 d . . . . .
C8 C 0.15188(14) 0.3550(3) 0.41469(14) 0.0418(5) Uani 1 1 d . . . . .
C9 C 0.17145(17) 0.5525(4) 0.37673(16) 0.0561(6) Uani 1 1 d . . . . .
H9 H 0.200817 0.659911 0.416591 0.067 Uiso 1 1 calc R U . . .
C10 C 0.1478(2) 0.5928(4) 0.27968(18) 0.0685(7) Uani 1 1 d . . . . .
H10 H 0.161992 0.726006 0.254872 0.082 Uiso 1 1 calc R U . . .
C11 C 0.1034(2) 0.4357(5) 0.22042(17) 0.0701(7) Uani 1 1 d . . . . .
H11 H 0.086542 0.463016 0.155658 0.084 Uiso 1 1 calc R U . . .
C12 C 0.08403(19) 0.2383(4) 0.25710(16) 0.0655(7) Uani 1 1 d . . . . .
H12 H 0.054341 0.131534 0.217044 0.079 Uiso 1 1 calc R U . . .
C13 C 0.10849(16) 0.1979(4) 0.35320(15) 0.0516(6) Uani 1 1 d . . . . .
H13 H 0.095712 0.063209 0.377197 0.062 Uiso 1 1 calc R U . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0655(8) 0.0415(7) 0.0733(9) -0.0003(6) 0.0072(6) -0.0014(6)
O1 0.0624(11) 0.0795(13) 0.0975(13) -0.0315(11) 0.0345(10) -0.0236(9)
O2 0.0652(10) 0.0628(11) 0.0797(12) -0.0218(9) 0.0193(8) -0.0212(8)
C1 0.0483(12) 0.0411(12) 0.0453(12) -0.0009(10) 0.0029(9) -0.0057(10)
C2 0.0395(11) 0.0441(12) 0.0426(12) -0.0013(9) 0.0051(9) -0.0080(9)
C3 0.0516(13) 0.0663(15) 0.0542(13) 0.0011(11) 0.0087(10) -0.0177(11)
C4 0.0614(15) 0.0807(18) 0.0454(13) -0.0011(12) 0.0142(11) -0.0187(13)
C5 0.0672(15) 0.0706(16) 0.0468(13) 0.0115(12) 0.0001(11) -0.0135(13)
C6 0.0505(13) 0.0604(15) 0.0575(14) -0.0110(12) 0.0091(10) -0.0051(11)
C7 0.0411(12) 0.0521(14) 0.0411(12) -0.0023(10) 0.0003(9) -0.0003(10)
C8 0.0340(10) 0.0441(12) 0.0473(12) 0.0022(10) 0.0035(9) -0.0028(9)
C9 0.0565(14) 0.0518(14) 0.0596(14) 0.0023(11) 0.0027(11) -0.0050(11)
C10 0.0735(17) 0.0646(17) 0.0677(17) 0.0233(15) 0.0082(13) 0.0021(13)
C11 0.0700(16) 0.089(2) 0.0499(14) 0.0142(15) -0.0020(12) 0.0090(15)
C12 0.0656(16) 0.0782(19) 0.0504(14) -0.0035(13) -0.0059(12) -0.0085(13)
C13 0.0502(13) 0.0521(14) 0.0519(13) 0.0010(11) 0.0021(10) -0.0087(11)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C1 1.398(2) . ?
O1 H1 0.8200 . ?
O1 C7 1.241(2) . ?
O2 C7 1.261(2) . ?
C1 C2 1.542(3) . ?
C1 C5 1.538(3) . ?
C1 C7 1.515(3) . ?
C2 C3 1.561(3) . ?
C2 C6 1.557(3) . ?
C2 C8 1.494(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.538(3) . ?
C4 H4 0.9800 . ?
C4 C5 1.525(3) . ?
C4 C6 1.534(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C8 C9 1.381(3) . ?
C8 C13 1.388(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.390(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.374(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.373(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.379(3) . ?
C13 H13 0.9300 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O1 H1 109.5 . . ?
F1 C1 C2 109.22(15) . . ?
F1 C1 C5 110.32(17) . . ?
F1 C1 C7 106.41(16) . . ?
C5 C1 C2 100.22(16) . . ?
C7 C1 C2 115.17(17) . . ?
C7 C1 C5 115.39(17) . . ?
C1 C2 C3 99.50(16) . . ?
C1 C2 C6 101.66(16) . . ?
C6 C2 C3 84.87(15) . . ?
C8 C2 C1 118.42(16) . . ?
C8 C2 C3 121.58(16) . . ?
C8 C2 C6 123.87(18) . . ?
C2 C3 H3A 114.8 . . ?
C2 C3 H3B 114.8 . . ?
H3A C3 H3B 111.9 . . ?
C4 C3 C2 82.92(15) . . ?
C4 C3 H3A 114.8 . . ?
C4 C3 H3B 114.8 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 102.53(19) . . ?
C5 C4 H4 119.9 . . ?
C5 C4 C6 102.03(17) . . ?
C6 C4 C3 86.42(17) . . ?
C6 C4 H4 119.9 . . ?
C1 C5 H5A 112.0 . . ?
C1 C5 H5B 112.0 . . ?
C4 C5 C1 99.00(17) . . ?
C4 C5 H5A 112.0 . . ?
C4 C5 H5B 112.0 . . ?
H5A C5 H5B 109.7 . . ?
C2 C6 H6A 114.8 . . ?
C2 C6 H6B 114.8 . . ?
C4 C6 C2 83.16(16) . . ?
C4 C6 H6A 114.8 . . ?
C4 C6 H6B 114.8 . . ?
H6A C6 H6B 111.9 . . ?
O1 C7 O2 124.4(2) . . ?
O1 C7 C1 118.43(19) . . ?
O2 C7 C1 117.21(18) . . ?
C9 C8 C2 121.82(18) . . ?
C9 C8 C13 118.16(19) . . ?
C13 C8 C2 120.02(18) . . ?
C8 C9 H9 119.6 . . ?
C8 C9 C10 120.8(2) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 120.0(2) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.8(2) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.2(2) . . ?
C13 C12 H12 119.9 . . ?
C8 C13 H13 119.5 . . ?
C12 C13 C8 121.1(2) . . ?
C12 C13 H13 119.5 . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C1 C2 C3 70.04(18) . . . . ?
F1 C1 C2 C6 156.71(16) . . . . ?
F1 C1 C2 C8 -63.9(2) . . . . ?
F1 C1 C5 C4 -112.45(19) . . . . ?
F1 C1 C7 O1 9.4(3) . . . . ?
F1 C1 C7 O2 -171.13(17) . . . . ?
C1 C2 C3 C4 66.41(17) . . . . ?
C1 C2 C6 C4 -64.02(16) . . . . ?
C1 C2 C8 C9 -92.8(2) . . . . ?
C1 C2 C8 C13 87.9(2) . . . . ?
C2 C1 C5 C4 2.6(2) . . . . ?
C2 C1 C7 O1 -111.8(2) . . . . ?
C2 C1 C7 O2 67.7(2) . . . . ?
C2 C3 C4 C5 -66.47(18) . . . . ?
C2 C3 C4 C6 35.07(15) . . . . ?
C2 C8 C9 C10 -179.0(2) . . . . ?
C2 C8 C13 C12 178.37(19) . . . . ?
C3 C2 C6 C4 34.65(15) . . . . ?
C3 C2 C8 C9 143.6(2) . . . . ?
C3 C2 C8 C13 -35.7(3) . . . . ?
C3 C4 C5 C1 42.5(2) . . . . ?
C3 C4 C6 C2 -35.16(15) . . . . ?
C5 C1 C2 C3 -45.85(19) . . . . ?
C5 C1 C2 C6 40.83(19) . . . . ?
C5 C1 C2 C8 -179.82(17) . . . . ?
C5 C1 C7 O1 132.1(2) . . . . ?
C5 C1 C7 O2 -48.4(3) . . . . ?
C5 C4 C6 C2 66.90(17) . . . . ?
C6 C2 C3 C4 -34.58(16) . . . . ?
C6 C2 C8 C9 37.0(3) . . . . ?
C6 C2 C8 C13 -142.3(2) . . . . ?
C6 C4 C5 C1 -46.5(2) . . . . ?
C7 C1 C2 C3 -170.33(17) . . . . ?
C7 C1 C2 C6 -83.7(2) . . . . ?
C7 C1 C2 C8 55.7(2) . . . . ?
C7 C1 C5 C4 126.9(2) . . . . ?
C8 C2 C3 C4 -161.6(2) . . . . ?
C8 C2 C6 C4 159.61(18) . . . . ?
C8 C9 C10 C11 0.6(4) . . . . ?
C9 C8 C13 C12 -1.0(3) . . . . ?
C9 C10 C11 C12 -1.0(4) . . . . ?
C10 C11 C12 C13 0.3(4) . . . . ?
C11 C12 C13 C8 0.6(4) . . . . ?
C13 C8 C9 C10 0.3(3) . . . . ?
_shelx_res_file
;
TITL v26_a.res in P2(1)/n
v26.res
created by SHELXL-2016/6 at 11:23:46 on 19-Aug-2022
REM Old TITL v26 in P2(1)/n
REM SHELXT solution in P2(1)/n
REM R1 0.185, Rweak 0.019, Alpha 0.023, Orientation as input
REM Formula found by SHELXT: C13 O2 F
CELL 0.71073 12.625 6.2763 14.0505 90 95.59 90
ZERR 4 0.0027 0.0014 0.0031 0 0.014 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H F O
UNIT 52 52 4 8
L.S. 4 0 39
PLAN 5
SIZE 0.21 0.12 0.1
TEMP 23
CONF
BOND $H
list 4
MORE -1
fmap 2 53
acta
OMIT -2 50
REM
REM
REM
WGHT 0.054700 0.355000
FVAR 0.75269
F1 3 0.293313 0.011090 0.513939 11.00000 0.06549 0.04147 =
0.07331 -0.00026 0.00725 -0.00141
O1 4 0.436831 0.263037 0.471195 11.00000 0.06242 0.07953 =
0.09748 -0.03151 0.03445 -0.02356
AFIX 147
H1 2 0.486252 0.344599 0.464326 11.00000 -1.50000
AFIX 0
O2 4 0.394949 0.518969 0.569181 11.00000 0.06523 0.06281 =
0.07968 -0.02180 0.01928 -0.02119
C1 1 0.284114 0.212883 0.554494 11.00000 0.04833 0.04106 =
0.04532 -0.00093 0.00293 -0.00574
C2 1 0.174972 0.308865 0.518982 11.00000 0.03948 0.04406 =
0.04259 -0.00132 0.00507 -0.00799
C3 1 0.101487 0.160956 0.573014 11.00000 0.05158 0.06630 =
0.05416 0.00109 0.00872 -0.01772
AFIX 23
H3A 2 0.026014 0.191104 0.560999 11.00000 -1.20000
H3B 2 0.116407 0.009915 0.568327 11.00000 -1.20000
AFIX 0
C4 1 0.157558 0.271716 0.661691 11.00000 0.06143 0.08072 =
0.04545 -0.00114 0.01424 -0.01867
AFIX 13
H4 2 0.123531 0.275088 0.721455 11.00000 -1.20000
AFIX 0
C5 1 0.271908 0.193097 0.661996 11.00000 0.06719 0.07057 =
0.04682 0.01153 0.00005 -0.01346
AFIX 23
H5A 2 0.279788 0.047039 0.684126 11.00000 -1.20000
H5B 2 0.321705 0.283737 0.700171 11.00000 -1.20000
AFIX 0
C6 1 0.158362 0.472496 0.599452 11.00000 0.05050 0.06037 =
0.05750 -0.01100 0.00908 -0.00513
AFIX 23
H6A 2 0.218028 0.567447 0.615633 11.00000 -1.20000
H6B 2 0.091325 0.548977 0.591360 11.00000 -1.20000
AFIX 0
C7 1 0.379600 0.339960 0.529423 11.00000 0.04114 0.05214 =
0.04112 -0.00228 0.00033 -0.00025
C8 1 0.151875 0.354978 0.414685 11.00000 0.03400 0.04411 =
0.04727 0.00223 0.00350 -0.00283
C9 1 0.171450 0.552524 0.376733 11.00000 0.05647 0.05177 =
0.05959 0.00227 0.00272 -0.00503
AFIX 43
H9 2 0.200817 0.659911 0.416591 11.00000 -1.20000
AFIX 0
C10 1 0.147787 0.592789 0.279678 11.00000 0.07353 0.06464 =
0.06772 0.02327 0.00820 0.00208
AFIX 43
H10 2 0.161992 0.726006 0.254872 11.00000 -1.20000
AFIX 0
C11 1 0.103405 0.435694 0.220416 11.00000 0.06999 0.08892 =
0.04994 0.01415 -0.00203 0.00899
AFIX 43
H11 2 0.086542 0.463016 0.155658 11.00000 -1.20000
AFIX 0
C12 1 0.084030 0.238264 0.257101 11.00000 0.06562 0.07816 =
0.05040 -0.00351 -0.00590 -0.00848
AFIX 43
H12 2 0.054341 0.131534 0.217044 11.00000 -1.20000
AFIX 0
C13 1 0.108492 0.197892 0.353197 11.00000 0.05016 0.05213 =
0.05188 0.00100 0.00213 -0.00870
AFIX 43
H13 2 0.095712 0.063209 0.377197 11.00000 -1.20000
AFIX 0
HKLF 4
REM v26_a.res in P2(1)/n
REM R1 = 0.0474 for 1370 Fo > 4sig(Fo) and 0.0744 for all 1955 data
REM 146 parameters refined using 0 restraints
END
WGHT 0.0547 0.3546
REM Highest difference peak 0.159, deepest hole -0.177, 1-sigma level 0.039
Q1 1 0.5481 0.3765 0.4353 11.00000 0.05 0.16
Q2 1 0.3801 0.5336 0.5125 11.00000 0.05 0.15
Q3 1 0.2884 -0.0075 0.6586 11.00000 0.05 0.15
Q4 1 0.4175 0.4407 0.5814 11.00000 0.05 0.14
Q5 1 0.1525 0.3360 0.4693 11.00000 0.05 0.14
;
_shelx_res_checksum 74383
_olex2_submission_special_instructions 'No special instructions were received'
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_v109
_audit_block_doi 10.5517/ccdc.csd.cc2gr9vd
_database_code_depnum_ccdc_archive 'CCDC 2286524'
loop_
_citation_id
_citation_doi
_citation_year
1 10.26434/chemrxiv-2023-78z7p 2023
loop_
_audit_author_name
_audit_author_address
'Iryna Sadkova'
;Enamine Ltd
Ukraine
;
_audit_update_record
;
2023-08-03 deposited with the CCDC. 2023-10-27 downloaded from the CCDC.
;
_audit_creation_date 2023-03-08
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number 2016/6
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C14 H13 F3 O2'
_chemical_formula_sum 'C14 H13 F3 O2'
_chemical_formula_weight 270.24
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system monoclinic
_space_group_IT_number 14
_space_group_name_H-M_alt 'P 1 21/c 1'
_space_group_name_Hall '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a 7.9641(4)
_cell_length_b 20.6944(9)
_cell_length_c 8.0024(4)
_cell_angle_alpha 90
_cell_angle_beta 104.190(3)
_cell_angle_gamma 90
_cell_volume 1278.65(11)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 3974
_cell_measurement_temperature 296.15
_cell_measurement_theta_max 21.82
_cell_measurement_theta_min 2.64
_shelx_estimated_absorpt_T_max 0.981
_shelx_estimated_absorpt_T_min 0.973
_exptl_absorpt_coefficient_mu 0.122
_exptl_absorpt_correction_T_max ?
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_type none
_exptl_absorpt_process_details ?
_exptl_absorpt_special_details ?
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.404
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 560
_exptl_crystal_size_max 0.23
_exptl_crystal_size_mid 0.18
_exptl_crystal_size_min 0.16
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0411
_diffrn_reflns_av_unetI/netI 0.0254
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_k_max 24
_diffrn_reflns_limit_k_min -24
_diffrn_reflns_limit_l_max 9
_diffrn_reflns_limit_l_min -9
_diffrn_reflns_number 17996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full 24.999
_diffrn_reflns_theta_max 24.999
_diffrn_reflns_theta_min 1.968
_diffrn_ambient_temperature 296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type 'Bruker APEX-II CCD'
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source ?
_diffrn_source_current 30.0
_diffrn_source_power 1.2
_diffrn_source_voltage 40.0
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 1849
_reflns_number_total 2257
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement ?
_computing_data_collection ?
_computing_data_reduction ?
_computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement 'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max 0.431
_refine_diff_density_min -0.388
_refine_diff_density_rms 0.046
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.036
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 176
_refine_ls_number_reflns 2257
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0684
_refine_ls_R_factor_gt 0.0560
_refine_ls_restrained_S_all 1.036
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0563P)^2^+1.2150P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1342
_refine_ls_wR_factor_ref 0.1424
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
C1(H1), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
C2(H2A,H2B), C4(H4A,H4B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
C9(H9), C11(H11), C12(H12), C13(H13)
;
_atom_sites_solution_hydrogens mixed
_atom_sites_solution_primary dual
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.8672(2) 0.34720(14) 0.7404(3) 0.1083(10) Uani 1 1 d . . . . .
F2 F 0.8060(3) 0.25154(11) 0.7922(4) 0.1182(10) Uani 1 1 d . . . . .
F3 F 0.7700(3) 0.32647(13) 0.9545(2) 0.0940(8) Uani 1 1 d . . . . .
O1 O 0.0186(2) 0.48671(9) 0.3007(2) 0.0443(5) Uani 1 1 d . . . . .
O2 O 0.2293(2) 0.50262(9) 0.5382(2) 0.0404(5) Uani 1 1 d . . . . .
H2 H 0.139(5) 0.5068(18) 0.593(5) 0.093(12) Uiso 1 1 d . . . . .
C1 C 0.3150(3) 0.47543(11) 0.2858(3) 0.0320(5) Uani 1 1 d . . . . .
H1 H 0.426402 0.495041 0.351671 0.038 Uiso 1 1 calc R U . . .
C2 C 0.2793(3) 0.49481(12) 0.0924(3) 0.0405(6) Uani 1 1 d . . . . .
H2A H 0.160484 0.511806 0.048240 0.049 Uiso 1 1 calc R U . . .
H2B H 0.364288 0.526875 0.071849 0.049 Uiso 1 1 calc R U . . .
C3 C 0.3027(3) 0.42904(13) 0.0146(3) 0.0458(7) Uani 1 1 d . . . . .
H3 H 0.292692 0.425077 -0.112064 0.055 Uiso 1 1 calc R U . . .
C4 C 0.4641(3) 0.40092(14) 0.1456(3) 0.0420(6) Uani 1 1 d . . . . .
H4A H 0.501050 0.357646 0.115739 0.050 Uiso 1 1 calc R U . . .
H4B H 0.563025 0.431077 0.179966 0.050 Uiso 1 1 calc R U . . .
C5 C 0.1927(3) 0.38464(13) 0.1030(3) 0.0436(6) Uani 1 1 d . . . . .
H5A H 0.187294 0.338820 0.066565 0.052 Uiso 1 1 calc R U . . .
H5B H 0.076926 0.401853 0.103878 0.052 Uiso 1 1 calc R U . . .
C6 C 0.3381(3) 0.40053(11) 0.2668(3) 0.0325(5) Uani 1 1 d . . . . .
C7 C 0.1740(3) 0.48965(10) 0.3747(3) 0.0299(5) Uani 1 1 d . . . . .
C8 C 0.3713(3) 0.36209(11) 0.4304(3) 0.0306(5) Uani 1 1 d . . . . .
C9 C 0.5397(3) 0.35441(11) 0.5299(3) 0.0320(5) Uani 1 1 d . . . . .
H9 H 0.633708 0.372574 0.492256 0.038 Uiso 1 1 calc R U . . .
C10 C 0.5713(3) 0.32023(11) 0.6843(3) 0.0351(6) Uani 1 1 d . . . . .
C11 C 0.4352(3) 0.29361(12) 0.7409(3) 0.0405(6) Uani 1 1 d . . . . .
H11 H 0.456776 0.270522 0.846639 0.049 Uiso 1 1 calc R U . . .
C12 C 0.2678(3) 0.30103(12) 0.6418(3) 0.0435(6) Uani 1 1 d . . . . .
H12 H 0.173995 0.282966 0.679843 0.052 Uiso 1 1 calc R U . . .
C13 C 0.2357(3) 0.33471(11) 0.4869(3) 0.0372(6) Uani 1 1 d . . . . .
H13 H 0.120283 0.339043 0.419130 0.045 Uiso 1 1 calc R U . . .
C14 C 0.7513(4) 0.31148(14) 0.7907(3) 0.0470(7) Uani 1 1 d . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0413(11) 0.184(3) 0.0887(16) 0.0658(16) -0.0056(10) -0.0113(13)
F2 0.0891(16) 0.0805(15) 0.148(2) -0.0238(14) -0.0415(15) 0.0450(12)
F3 0.0683(13) 0.160(2) 0.0438(11) -0.0153(12) -0.0056(9) 0.0038(13)
O1 0.0304(10) 0.0684(12) 0.0329(10) -0.0018(8) 0.0056(7) 0.0059(8)
O2 0.0325(10) 0.0572(11) 0.0314(9) -0.0077(8) 0.0078(7) -0.0025(8)
C1 0.0280(12) 0.0385(13) 0.0283(12) 0.0017(10) 0.0049(9) -0.0021(10)
C2 0.0388(14) 0.0511(15) 0.0318(13) 0.0084(11) 0.0088(11) 0.0017(11)
C3 0.0514(16) 0.0609(17) 0.0247(12) 0.0011(11) 0.0085(11) 0.0069(13)
C4 0.0418(14) 0.0555(16) 0.0307(13) 0.0012(11) 0.0130(11) 0.0078(12)
C5 0.0427(15) 0.0479(15) 0.0355(14) -0.0072(11) 0.0008(11) -0.0002(12)
C6 0.0296(12) 0.0391(13) 0.0285(12) -0.0022(10) 0.0064(10) 0.0022(10)
C7 0.0294(13) 0.0310(12) 0.0278(12) 0.0022(9) 0.0040(10) 0.0006(9)
C8 0.0333(13) 0.0308(12) 0.0285(12) -0.0032(9) 0.0093(10) 0.0017(9)
C9 0.0321(13) 0.0326(12) 0.0321(12) -0.0022(9) 0.0096(10) -0.0022(9)
C10 0.0407(14) 0.0315(12) 0.0325(13) -0.0007(10) 0.0080(11) 0.0032(10)
C11 0.0534(16) 0.0346(13) 0.0359(14) 0.0054(10) 0.0153(12) 0.0031(11)
C12 0.0434(15) 0.0393(14) 0.0533(16) 0.0065(12) 0.0224(13) -0.0031(11)
C13 0.0318(13) 0.0375(13) 0.0425(14) 0.0003(11) 0.0093(11) 0.0008(10)
C14 0.0464(16) 0.0550(17) 0.0365(15) 0.0065(12) 0.0041(12) 0.0051(13)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C14 1.321(3) . ?
F2 C14 1.314(3) . ?
F3 C14 1.319(3) . ?
O1 C7 1.235(3) . ?
O2 H2 0.94(4) . ?
O2 C7 1.302(3) . ?
C1 H1 1.0000 . ?
C1 C2 1.556(3) . ?
C1 C6 1.573(3) . ?
C1 C7 1.498(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.527(4) . ?
C3 H3 1.0000 . ?
C3 C4 1.558(4) . ?
C3 C5 1.555(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C6 1.557(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.556(3) . ?
C6 C8 1.499(3) . ?
C8 C9 1.391(3) . ?
C8 C13 1.389(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.392(3) . ?
C10 C11 1.388(3) . ?
C10 C14 1.488(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.382(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.390(4) . ?
C13 H13 0.9500 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O2 H2 112(2) . . ?
C2 C1 H1 110.0 . . ?
C2 C1 C6 98.90(18) . . ?
C6 C1 H1 110.0 . . ?
C7 C1 H1 110.0 . . ?
C7 C1 C2 116.48(19) . . ?
C7 C1 C6 111.01(18) . . ?
C1 C2 H2A 111.9 . . ?
C1 C2 H2B 111.9 . . ?
H2A C2 H2B 109.6 . . ?
C3 C2 C1 99.51(19) . . ?
C3 C2 H2A 111.9 . . ?
C3 C2 H2B 111.9 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 102.8(2) . . ?
C2 C3 C5 101.6(2) . . ?
C4 C3 H3 119.9 . . ?
C5 C3 H3 119.9 . . ?
C5 C3 C4 86.37(19) . . ?
C3 C4 H4A 114.9 . . ?
C3 C4 H4B 114.9 . . ?
H4A C4 H4B 111.9 . . ?
C6 C4 C3 82.54(17) . . ?
C6 C4 H4A 114.9 . . ?
C6 C4 H4B 114.9 . . ?
C3 C5 H5A 114.9 . . ?
C3 C5 H5B 114.9 . . ?
C3 C5 C6 82.68(18) . . ?
H5A C5 H5B 111.9 . . ?
C6 C5 H5A 114.9 . . ?
C6 C5 H5B 114.9 . . ?
C4 C6 C1 99.42(19) . . ?
C5 C6 C1 102.09(18) . . ?
C5 C6 C4 86.37(18) . . ?
C8 C6 C1 115.97(18) . . ?
C8 C6 C4 122.96(19) . . ?
C8 C6 C5 124.0(2) . . ?
O1 C7 O2 123.0(2) . . ?
O1 C7 C1 122.8(2) . . ?
O2 C7 C1 114.13(19) . . ?
C9 C8 C6 120.0(2) . . ?
C13 C8 C6 121.0(2) . . ?
C13 C8 C9 119.0(2) . . ?
C8 C9 H9 119.8 . . ?
C8 C9 C10 120.3(2) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 C14 120.6(2) . . ?
C11 C10 C9 120.4(2) . . ?
C11 C10 C14 119.0(2) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 C10 119.3(2) . . ?
C12 C11 H11 120.4 . . ?
C11 C12 H12 119.7 . . ?
C11 C12 C13 120.5(2) . . ?
C13 C12 H12 119.7 . . ?
C8 C13 C12 120.4(2) . . ?
C8 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
F1 C14 C10 113.9(2) . . ?
F2 C14 F1 106.0(3) . . ?
F2 C14 F3 104.9(2) . . ?
F2 C14 C10 113.0(2) . . ?
F3 C14 F1 104.7(3) . . ?
F3 C14 C10 113.5(2) . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -41.4(2) . . . . ?
C1 C2 C3 C5 47.5(2) . . . . ?
C1 C6 C8 C9 -86.9(3) . . . . ?
C1 C6 C8 C13 91.9(3) . . . . ?
C2 C1 C6 C4 47.6(2) . . . . ?
C2 C1 C6 C5 -40.7(2) . . . . ?
C2 C1 C6 C8 -178.47(19) . . . . ?
C2 C1 C7 O1 34.1(3) . . . . ?
C2 C1 C7 O2 -148.7(2) . . . . ?
C2 C3 C4 C6 66.7(2) . . . . ?
C2 C3 C5 C6 -67.9(2) . . . . ?
C3 C4 C6 C1 -67.26(19) . . . . ?
C3 C4 C6 C5 34.41(18) . . . . ?
C3 C4 C6 C8 163.2(2) . . . . ?
C3 C5 C6 C1 64.39(19) . . . . ?
C3 C5 C6 C4 -34.48(18) . . . . ?
C3 C5 C6 C8 -162.4(2) . . . . ?
C4 C3 C5 C6 34.45(17) . . . . ?
C4 C6 C8 C9 35.3(3) . . . . ?
C4 C6 C8 C13 -145.9(2) . . . . ?
C5 C3 C4 C6 -34.44(18) . . . . ?
C5 C6 C8 C9 145.6(2) . . . . ?
C5 C6 C8 C13 -35.6(3) . . . . ?
C6 C1 C2 C3 -3.7(2) . . . . ?
C6 C1 C7 O1 -78.0(3) . . . . ?
C6 C1 C7 O2 99.1(2) . . . . ?
C6 C8 C9 C10 178.3(2) . . . . ?
C6 C8 C13 C12 -177.8(2) . . . . ?
C7 C1 C2 C3 -122.6(2) . . . . ?
C7 C1 C6 C4 170.49(18) . . . . ?
C7 C1 C6 C5 82.2(2) . . . . ?
C7 C1 C6 C8 -55.5(3) . . . . ?
C8 C9 C10 C11 -0.2(3) . . . . ?
C8 C9 C10 C14 179.6(2) . . . . ?
C9 C8 C13 C12 1.0(3) . . . . ?
C9 C10 C11 C12 0.4(4) . . . . ?
C9 C10 C14 F1 10.6(4) . . . . ?
C9 C10 C14 F2 -110.4(3) . . . . ?
C9 C10 C14 F3 130.3(3) . . . . ?
C10 C11 C12 C13 0.1(4) . . . . ?
C11 C10 C14 F1 -169.6(3) . . . . ?
C11 C10 C14 F2 69.4(3) . . . . ?
C11 C10 C14 F3 -49.9(3) . . . . ?
C11 C12 C13 C8 -0.8(4) . . . . ?
C13 C8 C9 C10 -0.5(3) . . . . ?
C14 C10 C11 C12 -179.4(2) . . . . ?
_shelx_res_file
;
TITL v109_a.res in P2(1)/c
v109.res
created by SHELXL-2016/6 at 15:48:27 on 08-Mar-2023
REM Old TITL v109 in P2(1)/c
REM SHELXT solution in P2(1)/c
REM R1 0.200, Rweak 0.014, Alpha 0.032, Orientation as input
REM Formula found by SHELXT: C14 O2 F3
CELL 0.71073 7.9641 20.6944 8.0024 90 104.19 90
ZERR 4 0.0004 0.0009 0.0004 0 0.003 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H F O
UNIT 56 52 12 8
L.S. 4
PLAN 5
SIZE 0.23 0.18 0.16
TEMP -100.5
CONF
BOND $H
list 4
MORE -1
fmap 2
acta
OMIT -2 50
REM
REM
REM
WGHT 0.056300 1.215000
FVAR 0.70231
F1 3 0.867245 0.347204 0.740368 11.00000 0.04131 0.18367 =
0.08865 0.06584 -0.00564 -0.01134
F2 3 0.805984 0.251543 0.792168 11.00000 0.08906 0.08047 =
0.14833 -0.02380 -0.04153 0.04503
F3 3 0.770025 0.326474 0.954487 11.00000 0.06828 0.15979 =
0.04384 -0.01527 -0.00564 0.00385
O1 4 0.018632 0.486705 0.300678 11.00000 0.03038 0.06841 =
0.03291 -0.00176 0.00561 0.00585
O2 4 0.229339 0.502621 0.538194 11.00000 0.03252 0.05720 =
0.03138 -0.00768 0.00780 -0.00252
H2 2 0.138569 0.506757 0.593074 11.00000 0.09275
C1 1 0.315019 0.475429 0.285844 11.00000 0.02804 0.03849 =
0.02830 0.00171 0.00491 -0.00207
AFIX 13
H1 2 0.426402 0.495041 0.351671 11.00000 -1.20000
AFIX 0
C2 1 0.279303 0.494813 0.092428 11.00000 0.03882 0.05114 =
0.03175 0.00840 0.00878 0.00173
AFIX 23
H2A 2 0.160484 0.511806 0.048240 11.00000 -1.20000
H2B 2 0.364288 0.526875 0.071849 11.00000 -1.20000
AFIX 0
C3 1 0.302734 0.429038 0.014550 11.00000 0.05143 0.06090 =
0.02471 0.00112 0.00855 0.00690
AFIX 13
H3 2 0.292692 0.425077 -0.112064 11.00000 -1.20000
AFIX 0
C4 1 0.464063 0.400919 0.145555 11.00000 0.04180 0.05552 =
0.03066 0.00122 0.01296 0.00781
AFIX 23
H4A 2 0.501050 0.357646 0.115739 11.00000 -1.20000
H4B 2 0.563025 0.431077 0.179966 11.00000 -1.20000
AFIX 0
C5 1 0.192703 0.384642 0.103049 11.00000 0.04274 0.04791 =
0.03554 -0.00717 0.00079 -0.00021
AFIX 23
H5A 2 0.187294 0.338820 0.066565 11.00000 -1.20000
H5B 2 0.076926 0.401853 0.103878 11.00000 -1.20000
AFIX 0
C6 1 0.338067 0.400527 0.266776 11.00000 0.02961 0.03907 =
0.02847 -0.00223 0.00645 0.00218
C7 1 0.173995 0.489654 0.374707 11.00000 0.02936 0.03100 =
0.02776 0.00217 0.00404 0.00057
C8 1 0.371336 0.362091 0.430428 11.00000 0.03330 0.03081 =
0.02854 -0.00322 0.00929 0.00171
C9 1 0.539749 0.354405 0.529888 11.00000 0.03206 0.03261 =
0.03209 -0.00224 0.00960 -0.00221
AFIX 43
H9 2 0.633708 0.372574 0.492256 11.00000 -1.20000
AFIX 0
C10 1 0.571345 0.320235 0.684262 11.00000 0.04074 0.03149 =
0.03250 -0.00072 0.00795 0.00318
C11 1 0.435196 0.293605 0.740895 11.00000 0.05343 0.03460 =
0.03585 0.00539 0.01531 0.00309
AFIX 43
H11 2 0.456776 0.270522 0.846639 11.00000 -1.20000
AFIX 0
C12 1 0.267826 0.301029 0.641783 11.00000 0.04341 0.03925 =
0.05332 0.00649 0.02243 -0.00310
AFIX 43
H12 2 0.173995 0.282966 0.679843 11.00000 -1.20000
AFIX 0
C13 1 0.235708 0.334715 0.486853 11.00000 0.03178 0.03746 =
0.04248 0.00030 0.00935 0.00076
AFIX 43
H13 2 0.120283 0.339043 0.419130 11.00000 -1.20000
AFIX 0
C14 1 0.751255 0.311485 0.790744 11.00000 0.04639 0.05501 =
0.03652 0.00649 0.00414 0.00506
HKLF 4
REM v109_a.res in P2(1)/c
REM R1 = 0.0560 for 1849 Fo > 4sig(Fo) and 0.0684 for all 2257 data
REM 176 parameters refined using 0 restraints
END
WGHT 0.0561 1.2164
REM Highest difference peak 0.431, deepest hole -0.388, 1-sigma level 0.046
Q1 1 0.7661 0.2746 0.9100 11.00000 0.05 0.43
Q2 1 0.8477 0.2956 0.6894 11.00000 0.05 0.43
Q3 1 0.8025 0.3607 0.8550 11.00000 0.05 0.42
Q4 1 0.3531 0.3773 0.3481 11.00000 0.05 0.23
Q5 1 0.7894 0.2348 0.8015 11.00000 0.05 0.23
;
_shelx_res_checksum 53148
_olex2_submission_special_instructions 'No special instructions were received'
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_v123
_audit_block_doi 10.5517/ccdc.csd.cc2gr9tc
_database_code_depnum_ccdc_archive 'CCDC 2286523'
loop_
_citation_id
_citation_doi
_citation_year
1 10.26434/chemrxiv-2023-78z7p 2023
loop_
_audit_author_name
_audit_author_address
'Iryna Sadkova'
;Enamine Ltd
Ukraine
;
_audit_update_record
;
2023-08-03 deposited with the CCDC. 2023-10-27 downloaded from the CCDC.
;
_audit_creation_date 2023-03-21
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number 2016/6
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety '0.5(C18 H16 Cl2 N2 O), 0.5(H2 O)'
_chemical_formula_sum 'C9 H9 Cl N O'
_chemical_formula_weight 182.62
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system monoclinic
_space_group_IT_number 15
_space_group_name_H-M_alt 'C 1 2/c 1'
_space_group_name_Hall '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
_cell_length_a 18.3768(13)
_cell_length_b 6.9898(4)
_cell_length_c 27.6891(17)
_cell_angle_alpha 90
_cell_angle_beta 103.554(7)
_cell_angle_gamma 90
_cell_volume 3457.6(4)
_cell_formula_units_Z 16
_cell_measurement_reflns_used 9067
_cell_measurement_temperature 273.15
_cell_measurement_theta_max 30.55
_cell_measurement_theta_min 2.28
_shelx_estimated_absorpt_T_max 0.955
_shelx_estimated_absorpt_T_min 0.926
_exptl_absorpt_coefficient_mu 0.388
_exptl_absorpt_correction_T_max ?
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_type none
_exptl_absorpt_process_details ?
_exptl_absorpt_special_details ?
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.403
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 1520
_exptl_crystal_size_max 0.2
_exptl_crystal_size_mid 0.2
_exptl_crystal_size_min 0.12
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0833
_diffrn_reflns_av_unetI/netI 0.0575
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max 25
_diffrn_reflns_limit_h_min -25
_diffrn_reflns_limit_k_max 9
_diffrn_reflns_limit_k_min -9
_diffrn_reflns_limit_l_max 38
_diffrn_reflns_limit_l_min -38
_diffrn_reflns_number 29127
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 29.999
_diffrn_reflns_theta_min 2.280
_diffrn_ambient_temperature 273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type 'Bruker APEX-II CCD'
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source ?
_diffrn_source_current 30.0
_diffrn_source_power 1.2
_diffrn_source_voltage 40.0
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 3730
_reflns_number_total 5031
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement ?
_computing_data_collection ?
_computing_data_reduction ?
_computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement 'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max 0.553
_refine_diff_density_min -0.416
_refine_diff_density_rms 0.073
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.106
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 224
_refine_ls_number_reflns 5031
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.1055
_refine_ls_R_factor_gt 0.0719
_refine_ls_restrained_S_all 1.106
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+11.7087P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1328
_refine_ls_wR_factor_ref 0.1447
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups
At 1.5 times of:
All O(H,H) groups
2.a Free rotating group:
O1W(H1WA,H1WB)
2.b Ternary CH refined with riding coordinates:
C4(H4), C6(H6)
2.c Secondary CH2 refined with riding coordinates:
C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B)
2.d Aromatic/amide H refined with riding coordinates:
C9(H9), C10(H10), C11(H11), C14(H14), C15(H15), C17(H17), C18(H18)
;
_atom_sites_solution_hydrogens mixed
_atom_sites_solution_primary dual
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.57711(13) 0.1180(3) 0.65634(9) 0.0207(5) Uani 1 1 d . . . . .
C2 C 0.52842(14) -0.0579(4) 0.63455(10) 0.0261(5) Uani 1 1 d . . . . .
H2A H 0.522086 -0.076482 0.599096 0.031 Uiso 1 1 calc R U . . .
H2B H 0.541455 -0.175984 0.652932 0.031 Uiso 1 1 calc R U . . .
C3 C 0.52699(16) 0.1305(4) 0.69451(10) 0.0295(6) Uani 1 1 d . . . . .
H3A H 0.539819 0.040737 0.721918 0.035 Uiso 1 1 calc R U . . .
H3B H 0.519490 0.258799 0.705756 0.035 Uiso 1 1 calc R U . . .
C4 C 0.46556(15) 0.0598(4) 0.64943(10) 0.0283(6) Uani 1 1 d . . . . .
H4 H 0.420753 -0.004598 0.654819 0.034 Uiso 1 1 calc R U . . .
C5 C 0.45794(14) 0.2288(4) 0.61351(11) 0.0291(6) Uani 1 1 d . . . . .
H5A H 0.429347 0.332805 0.623105 0.035 Uiso 1 1 calc R U . . .
H5B H 0.435587 0.191019 0.579558 0.035 Uiso 1 1 calc R U . . .
C6 C 0.54216(13) 0.2810(4) 0.62091(9) 0.0212(5) Uani 1 1 d . . . . .
H6 H 0.552016 0.403880 0.638276 0.025 Uiso 1 1 calc R U . . .
C7 C 0.59735(13) 0.4476(3) 0.56121(9) 0.0194(5) Uani 1 1 d . . . . .
C8 C 0.63485(13) 0.4275(3) 0.51849(9) 0.0187(4) Uani 1 1 d . . . . .
C9 C 0.59754(14) 0.3487(4) 0.47342(9) 0.0240(5) Uani 1 1 d . . . . .
H9 H 0.549089 0.302040 0.469357 0.029 Uiso 1 1 calc R U . . .
C10 C 0.63319(16) 0.3403(4) 0.43453(10) 0.0289(6) Uani 1 1 d . . . . .
H10 H 0.609010 0.289490 0.403942 0.035 Uiso 1 1 calc R U . . .
C11 C 0.70524(16) 0.4091(4) 0.44226(10) 0.0303(6) Uani 1 1 d . . . . .
H11 H 0.728929 0.403441 0.416072 0.036 Uiso 1 1 calc R U . . .
C12 C 0.70773(13) 0.4918(3) 0.52202(9) 0.0194(5) Uani 1 1 d . . . . .
C13 C 0.66098(14) 0.1132(4) 0.67181(9) 0.0231(5) Uani 1 1 d . . . . .
C14 C 0.70001(16) 0.2734(4) 0.69291(11) 0.0354(7) Uani 1 1 d . . . . .
H14 H 0.673709 0.383085 0.697372 0.042 Uiso 1 1 calc R U . . .
C15 C 0.77794(17) 0.2739(5) 0.70762(12) 0.0403(7) Uani 1 1 d . . . . .
H15 H 0.803741 0.382387 0.721667 0.048 Uiso 1 1 calc R U . . .
C16 C 0.81559(15) 0.1106(5) 0.70086(10) 0.0318(6) Uani 1 1 d . . . . .
C17 C 0.77892(16) -0.0512(4) 0.68000(10) 0.0326(6) Uani 1 1 d . . . . .
H17 H 0.805632 -0.160432 0.675711 0.039 Uiso 1 1 calc R U . . .
C18 C 0.70086(15) -0.0493(4) 0.66531(10) 0.0268(5) Uani 1 1 d . . . . .
H18 H 0.675414 -0.157914 0.651039 0.032 Uiso 1 1 calc R U . . .
Cl1 Cl 0.76022(4) 0.58193(10) 0.57790(3) 0.03066(16) Uani 1 1 d . . . . .
Cl2 Cl 0.91341(4) 0.11088(14) 0.71861(3) 0.0506(2) Uani 1 1 d . . . . .
N1 N 0.57131(11) 0.2857(3) 0.57617(8) 0.0196(4) Uani 1 1 d . . . . .
N2 N 0.74322(12) 0.4838(3) 0.48564(8) 0.0251(5) Uani 1 1 d . . . . .
O1 O 0.59171(11) 0.6059(3) 0.57937(8) 0.0306(4) Uani 1 1 d . . . . .
O1W O 0.60658(11) 0.9444(3) 0.52766(8) 0.0308(4) Uani 1 1 d G . . . .
H1WA H 0.605901 0.839546 0.543119 0.046 Uiso 1 1 d G U . . .
H1WB H 0.647604 0.941717 0.518481 0.046 Uiso 1 1 d G U . . .
H1 H 0.5822(15) 0.177(4) 0.5641(10) 0.017(7) Uiso 1 1 d . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0249(11) 0.0204(12) 0.0204(11) -0.0011(9) 0.0129(9) 0.0005(9)
C2 0.0289(13) 0.0182(12) 0.0351(14) 0.0008(11) 0.0155(11) -0.0008(10)
C3 0.0364(14) 0.0326(15) 0.0256(13) 0.0024(11) 0.0196(11) 0.0014(11)
C4 0.0264(13) 0.0273(14) 0.0366(14) 0.0018(11) 0.0182(11) -0.0016(10)
C5 0.0240(12) 0.0320(15) 0.0353(14) 0.0028(12) 0.0152(11) 0.0032(11)
C6 0.0254(12) 0.0190(12) 0.0227(12) -0.0018(9) 0.0128(9) -0.0002(9)
C7 0.0162(10) 0.0182(12) 0.0247(11) 0.0016(9) 0.0068(8) -0.0002(8)
C8 0.0213(11) 0.0127(11) 0.0234(11) 0.0026(9) 0.0080(9) 0.0033(9)
C9 0.0235(12) 0.0208(12) 0.0266(13) 0.0015(10) 0.0037(10) 0.0009(9)
C10 0.0421(15) 0.0259(14) 0.0185(12) 0.0021(10) 0.0065(11) 0.0029(11)
C11 0.0424(15) 0.0267(14) 0.0270(13) 0.0091(11) 0.0184(11) 0.0065(12)
C12 0.0210(11) 0.0135(11) 0.0248(11) 0.0032(9) 0.0074(9) 0.0014(8)
C13 0.0251(12) 0.0287(13) 0.0169(11) 0.0014(10) 0.0078(9) 0.0001(10)
C14 0.0310(14) 0.0333(16) 0.0402(16) -0.0115(13) 0.0048(12) 0.0028(12)
C15 0.0333(15) 0.0436(18) 0.0397(17) -0.0111(14) 0.0001(12) -0.0071(13)
C16 0.0232(12) 0.0488(18) 0.0209(12) 0.0023(12) 0.0001(9) -0.0002(12)
C17 0.0299(14) 0.0366(16) 0.0320(14) 0.0037(12) 0.0084(11) 0.0085(12)
C18 0.0272(13) 0.0273(14) 0.0261(12) 0.0017(11) 0.0068(10) 0.0011(10)
Cl1 0.0241(3) 0.0313(4) 0.0360(3) -0.0062(3) 0.0057(2) -0.0044(3)
Cl2 0.0249(3) 0.0699(6) 0.0507(5) 0.0044(4) -0.0040(3) 0.0016(4)
N1 0.0243(10) 0.0141(10) 0.0230(10) -0.0013(8) 0.0107(8) -0.0009(8)
N2 0.0280(11) 0.0207(11) 0.0308(12) 0.0057(9) 0.0154(9) 0.0018(9)
O1 0.0395(11) 0.0157(9) 0.0452(12) -0.0042(8) 0.0270(9) -0.0028(8)
O1W 0.0323(10) 0.0216(10) 0.0446(12) 0.0024(8) 0.0214(9) 0.0020(8)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.556(4) . ?
C1 C3 1.559(3) . ?
C1 C6 1.542(3) . ?
C1 C13 1.500(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C4 1.550(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.554(4) . ?
C4 H4 0.9800 . ?
C4 C5 1.529(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.556(3) . ?
C6 H6 0.9800 . ?
C6 N1 1.461(3) . ?
C7 C8 1.509(3) . ?
C7 N1 1.332(3) . ?
C7 O1 1.229(3) . ?
C8 C9 1.389(3) . ?
C8 C12 1.394(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.386(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.377(4) . ?
C11 H11 0.9300 . ?
C11 N2 1.345(4) . ?
C12 Cl1 1.738(3) . ?
C12 N2 1.323(3) . ?
C13 C14 1.383(4) . ?
C13 C18 1.386(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.394(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.370(4) . ?
C16 C17 1.373(4) . ?
C16 Cl2 1.749(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.396(4) . ?
C18 H18 0.9300 . ?
N1 H1 0.87(3) . ?
O1W H1WA 0.8502 . ?
O1W H1WB 0.8505 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C3 85.97(19) . . ?
C6 C1 C2 102.8(2) . . ?
C6 C1 C3 99.55(19) . . ?
C13 C1 C2 123.5(2) . . ?
C13 C1 C3 122.6(2) . . ?
C13 C1 C6 116.4(2) . . ?
C1 C2 H2A 114.8 . . ?
C1 C2 H2B 114.8 . . ?
H2A C2 H2B 111.9 . . ?
C4 C2 C1 82.79(18) . . ?
C4 C2 H2A 114.8 . . ?
C4 C2 H2B 114.8 . . ?
C1 C3 H3A 114.9 . . ?
C1 C3 H3B 114.9 . . ?
H3A C3 H3B 111.9 . . ?
C4 C3 C1 82.59(18) . . ?
C4 C3 H3A 114.9 . . ?
C4 C3 H3B 114.9 . . ?
C2 C4 C3 86.3(2) . . ?
C2 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C2 101.4(2) . . ?
C5 C4 C3 102.4(2) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5A 111.9 . . ?
C4 C5 H5B 111.9 . . ?
C4 C5 C6 99.1(2) . . ?
H5A C5 H5B 109.6 . . ?
C6 C5 H5A 111.9 . . ?
C6 C5 H5B 111.9 . . ?
C1 C6 C5 99.40(19) . . ?
C1 C6 H6 109.5 . . ?
C5 C6 H6 109.5 . . ?
N1 C6 C1 112.04(19) . . ?
N1 C6 C5 116.4(2) . . ?
N1 C6 H6 109.5 . . ?
N1 C7 C8 115.3(2) . . ?
O1 C7 C8 120.2(2) . . ?
O1 C7 N1 124.5(2) . . ?
C9 C8 C7 121.4(2) . . ?
C9 C8 C12 117.0(2) . . ?
C12 C8 C7 121.5(2) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 C8 119.4(2) . . ?
C10 C9 H9 120.3 . . ?
C9 C10 H10 120.8 . . ?
C11 C10 C9 118.5(2) . . ?
C11 C10 H10 120.8 . . ?
C10 C11 H11 118.2 . . ?
N2 C11 C10 123.6(2) . . ?
N2 C11 H11 118.2 . . ?
C8 C12 Cl1 120.18(18) . . ?
N2 C12 C8 124.7(2) . . ?
N2 C12 Cl1 115.03(18) . . ?
C14 C13 C1 119.9(2) . . ?
C14 C13 C18 118.7(2) . . ?
C18 C13 C1 121.4(2) . . ?
C13 C14 H14 119.3 . . ?
C13 C14 C15 121.4(3) . . ?
C15 C14 H14 119.3 . . ?
C14 C15 H15 120.8 . . ?
C16 C15 C14 118.4(3) . . ?
C16 C15 H15 120.8 . . ?
C15 C16 C17 122.0(3) . . ?
C15 C16 Cl2 118.6(2) . . ?
C17 C16 Cl2 119.4(2) . . ?
C16 C17 H17 120.5 . . ?
C16 C17 C18 118.9(3) . . ?
C18 C17 H17 120.5 . . ?
C13 C18 C17 120.6(3) . . ?
C13 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C6 N1 H1 118.0(18) . . ?
C7 N1 C6 120.8(2) . . ?
C7 N1 H1 119.2(18) . . ?
C12 N2 C11 116.8(2) . . ?
H1WA O1W H1WB 104.5 . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C4 C3 -34.73(18) . . . . ?
C1 C2 C4 C5 67.2(2) . . . . ?
C1 C3 C4 C2 34.69(18) . . . . ?
C1 C3 C4 C5 -66.2(2) . . . . ?
C1 C6 N1 C7 -129.6(2) . . . . ?
C1 C13 C14 C15 -179.9(3) . . . . ?
C1 C13 C18 C17 -179.9(2) . . . . ?
C2 C1 C3 C4 -34.56(18) . . . . ?
C2 C1 C6 C5 40.1(2) . . . . ?
C2 C1 C6 N1 -83.5(2) . . . . ?
C2 C1 C13 C14 -177.1(2) . . . . ?
C2 C1 C13 C18 3.1(4) . . . . ?
C2 C4 C5 C6 -47.7(2) . . . . ?
C3 C1 C2 C4 34.64(19) . . . . ?
C3 C1 C6 C5 -47.9(2) . . . . ?
C3 C1 C6 N1 -171.5(2) . . . . ?
C3 C1 C13 C14 -68.3(3) . . . . ?
C3 C1 C13 C18 111.9(3) . . . . ?
C3 C4 C5 C6 41.0(2) . . . . ?
C4 C5 C6 C1 4.2(2) . . . . ?
C4 C5 C6 N1 124.6(2) . . . . ?
C5 C6 N1 C7 117.0(3) . . . . ?
C6 C1 C2 C4 -64.2(2) . . . . ?
C6 C1 C3 C4 67.7(2) . . . . ?
C6 C1 C13 C14 54.2(3) . . . . ?
C6 C1 C13 C18 -125.6(3) . . . . ?
C7 C8 C9 C10 177.3(2) . . . . ?
C7 C8 C12 Cl1 4.8(3) . . . . ?
C7 C8 C12 N2 -177.9(2) . . . . ?
C8 C7 N1 C6 172.4(2) . . . . ?
C8 C9 C10 C11 0.7(4) . . . . ?
C8 C12 N2 C11 0.5(4) . . . . ?
C9 C8 C12 Cl1 -176.94(18) . . . . ?
C9 C8 C12 N2 0.4(4) . . . . ?
C9 C10 C11 N2 0.1(4) . . . . ?
C10 C11 N2 C12 -0.7(4) . . . . ?
C12 C8 C9 C10 -1.0(4) . . . . ?
C13 C1 C2 C4 161.6(2) . . . . ?
C13 C1 C3 C4 -162.3(2) . . . . ?
C13 C1 C6 C5 178.2(2) . . . . ?
C13 C1 C6 N1 54.6(3) . . . . ?
C13 C14 C15 C16 -0.2(5) . . . . ?
C14 C13 C18 C17 0.3(4) . . . . ?
C14 C15 C16 C17 0.3(5) . . . . ?
C14 C15 C16 Cl2 179.3(2) . . . . ?
C15 C16 C17 C18 -0.1(4) . . . . ?
C16 C17 C18 C13 -0.2(4) . . . . ?
C18 C13 C14 C15 -0.1(4) . . . . ?
Cl1 C12 N2 C11 177.89(19) . . . . ?
Cl2 C16 C17 C18 -179.1(2) . . . . ?
N1 C7 C8 C9 57.2(3) . . . . ?
N1 C7 C8 C12 -124.6(2) . . . . ?
O1 C7 C8 C9 -122.0(3) . . . . ?
O1 C7 C8 C12 56.2(3) . . . . ?
O1 C7 N1 C6 -8.5(4) . . . . ?
_shelx_res_file
;
TITL v123_a.res in C2/c
v123.res
created by SHELXL-2016/6 at 15:46:02 on 21-Mar-2023
REM Old TITL v123 in C2/c
REM SHELXT solution in C2/c
REM R1 0.146, Rweak 0.012, Alpha 0.033, Orientation as input
REM Formula found by SHELXT: C18 N2 O2 Cl2
CELL 0.71073 18.3768 6.9898 27.6891 90 103.554 90
ZERR 16 0.0013 0.0004 0.0017 0 0.007 0
LATT 7
SYMM -X,+Y,0.5-Z
SFAC C H Cl N O
UNIT 144 144 16 16 16
L.S. 4 0 0
PLAN 1
SIZE 0.2 0.2 0.12
TEMP 0
CONF
BOND $H
list 4
MORE -1
fmap 2 53
acta
OMIT -2 60
OMIT 0 0 2
REM
REM
REM
WGHT 0.030000 11.708700
FVAR 0.24171
C1 1 0.577106 0.117972 0.656340 11.00000 0.02490 0.02039 =
0.02044 -0.00110 0.01292 0.00051
C2 1 0.528418 -0.057861 0.634554 11.00000 0.02892 0.01822 =
0.03513 0.00083 0.01545 -0.00079
AFIX 23
H2A 2 0.522086 -0.076482 0.599096 11.00000 -1.20000
H2B 2 0.541455 -0.175984 0.652932 11.00000 -1.20000
AFIX 0
C3 1 0.526992 0.130453 0.694510 11.00000 0.03641 0.03264 =
0.02557 0.00239 0.01957 0.00136
AFIX 23
H3A 2 0.539819 0.040737 0.721918 11.00000 -1.20000
H3B 2 0.519490 0.258799 0.705756 11.00000 -1.20000
AFIX 0
C4 1 0.465556 0.059806 0.649430 11.00000 0.02639 0.02731 =
0.03656 0.00180 0.01816 -0.00159
AFIX 13
H4 2 0.420753 -0.004598 0.654819 11.00000 -1.20000
AFIX 0
C5 1 0.457935 0.228769 0.613506 11.00000 0.02403 0.03201 =
0.03533 0.00284 0.01522 0.00322
AFIX 23
H5A 2 0.429347 0.332805 0.623105 11.00000 -1.20000
H5B 2 0.435587 0.191019 0.579558 11.00000 -1.20000
AFIX 0
C6 1 0.542162 0.281035 0.620914 11.00000 0.02539 0.01900 =
0.02275 -0.00181 0.01276 -0.00022
AFIX 13
H6 2 0.552016 0.403880 0.638276 11.00000 -1.20000
AFIX 0
C7 1 0.597349 0.447634 0.561209 11.00000 0.01622 0.01825 =
0.02473 0.00159 0.00681 -0.00016
C8 1 0.634848 0.427499 0.518491 11.00000 0.02133 0.01274 =
0.02335 0.00264 0.00795 0.00330
C9 1 0.597538 0.348724 0.473416 11.00000 0.02354 0.02078 =
0.02657 0.00146 0.00369 0.00085
AFIX 43
H9 2 0.549089 0.302040 0.469357 11.00000 -1.20000
AFIX 0
C10 1 0.633191 0.340339 0.434535 11.00000 0.04206 0.02586 =
0.01847 0.00213 0.00649 0.00286
AFIX 43
H10 2 0.609010 0.289490 0.403942 11.00000 -1.20000
AFIX 0
C11 1 0.705242 0.409050 0.442264 11.00000 0.04238 0.02666 =
0.02700 0.00909 0.01840 0.00654
AFIX 43
H11 2 0.728929 0.403441 0.416072 11.00000 -1.20000
AFIX 0
C12 1 0.707731 0.491796 0.522021 11.00000 0.02098 0.01351 =
0.02485 0.00324 0.00744 0.00140
C13 1 0.660980 0.113185 0.671809 11.00000 0.02510 0.02872 =
0.01694 0.00138 0.00780 0.00009
C14 1 0.700010 0.273383 0.692906 11.00000 0.03105 0.03327 =
0.04016 -0.01152 0.00479 0.00275
AFIX 43
H14 2 0.673709 0.383085 0.697372 11.00000 -1.20000
AFIX 0
C15 1 0.777943 0.273880 0.707616 11.00000 0.03330 0.04364 =
0.03969 -0.01107 0.00010 -0.00707
AFIX 43
H15 2 0.803741 0.382387 0.721667 11.00000 -1.20000
AFIX 0
C16 1 0.815595 0.110566 0.700863 11.00000 0.02321 0.04879 =
0.02092 0.00227 0.00010 -0.00019
C17 1 0.778916 -0.051244 0.679996 11.00000 0.02986 0.03657 =
0.03198 0.00369 0.00837 0.00845
AFIX 43
H17 2 0.805632 -0.160432 0.675711 11.00000 -1.20000
AFIX 0
C18 1 0.700862 -0.049269 0.665309 11.00000 0.02720 0.02729 =
0.02610 0.00166 0.00684 0.00111
AFIX 43
H18 2 0.675414 -0.157914 0.651039 11.00000 -1.20000
AFIX 0
CL1 3 0.760216 0.581928 0.577899 11.00000 0.02408 0.03126 =
0.03598 -0.00620 0.00569 -0.00442
CL2 3 0.913409 0.110881 0.718608 11.00000 0.02485 0.06989 =
0.05067 0.00437 -0.00400 0.00158
N1 4 0.571312 0.285733 0.576169 11.00000 0.02435 0.01414 =
0.02296 -0.00130 0.01069 -0.00091
N2 4 0.743224 0.483840 0.485635 11.00000 0.02799 0.02075 =
0.03081 0.00571 0.01545 0.00179
O1 5 0.591709 0.605894 0.579367 11.00000 0.03947 0.01572 =
0.04520 -0.00416 0.02696 -0.00279
AFIX 6
O1W 5 0.606575 0.944383 0.527662 11.00000 0.03226 0.02161 =
0.04462 0.00237 0.02139 0.00199
H1WA 2 0.605901 0.839546 0.543119 11.00000 -1.50000
H1WB 2 0.647604 0.941717 0.518481 11.00000 -1.50000
AFIX 0
H1 2 0.582180 0.177463 0.564076 11.00000 0.01698
HKLF 4
REM v123_a.res in C2/c
REM R1 = 0.0719 for 3730 Fo > 4sig(Fo) and 0.1055 for all 5031 data
REM 224 parameters refined using 0 restraints
END
WGHT 0.0300 11.7089
REM Highest difference peak 0.553, deepest hole -0.416, 1-sigma level 0.073
Q1 1 0.7743 0.4641 0.5826 11.00000 0.05 0.55
;
_shelx_res_checksum 96115
_olex2_submission_special_instructions 'No special instructions were received'
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_vd29
_audit_block_doi 10.5517/ccdc.csd.cc2gr9wf
_database_code_depnum_ccdc_archive 'CCDC 2286525'
loop_
_citation_id
_citation_doi
_citation_year
1 10.26434/chemrxiv-2023-78z7p 2023
loop_
_audit_author_name
_audit_author_address
'Iryna Sadkova'
;Enamine Ltd
Ukraine
;
_audit_update_record
;
2023-08-03 deposited with the CCDC. 2023-10-27 downloaded from the CCDC.
;
_audit_creation_date 2022-09-02
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number 2016/6
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C14 H15 F O3'
_chemical_formula_sum 'C14 H15 F O3'
_chemical_formula_weight 250.26
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system monoclinic
_space_group_IT_number 14
_space_group_name_H-M_alt 'P 1 21/c 1'
_space_group_name_Hall '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a 9.5011(14)
_cell_length_b 11.9938(15)
_cell_length_c 11.5637(17)
_cell_angle_alpha 90
_cell_angle_beta 109.290(7)
_cell_angle_gamma 90
_cell_volume 1243.8(3)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 3219
_cell_measurement_temperature 273.15
_cell_measurement_theta_max 22.30
_cell_measurement_theta_min 2.27
_shelx_estimated_absorpt_T_max 0.983
_shelx_estimated_absorpt_T_min 0.980
_exptl_absorpt_coefficient_mu 0.103
_exptl_absorpt_correction_T_max ?
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_type none
_exptl_absorpt_process_details ?
_exptl_absorpt_special_details ?
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.336
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 528
_exptl_crystal_size_max 0.2
_exptl_crystal_size_mid 0.18
_exptl_crystal_size_min 0.17
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0574
_diffrn_reflns_av_unetI/netI 0.0348
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_k_max 14
_diffrn_reflns_limit_k_min -14
_diffrn_reflns_limit_l_max 13
_diffrn_reflns_limit_l_min -13
_diffrn_reflns_number 15158
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full 25.000
_diffrn_reflns_theta_max 25.000
_diffrn_reflns_theta_min 2.271
_diffrn_ambient_temperature 273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type 'Bruker APEX-II CCD'
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source ?
_diffrn_source_current 30.0
_diffrn_source_power 1.2
_diffrn_source_voltage 40.0
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 1595
_reflns_number_total 2190
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement ?
_computing_data_collection ?
_computing_data_reduction ?
_computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement 'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution 'SHELXS (Sheldrick, 2008)'
_refine_diff_density_max 0.177
_refine_diff_density_min -0.235
_refine_diff_density_rms 0.040
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.046
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 165
_refine_ls_number_reflns 2190
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0675
_refine_ls_R_factor_gt 0.0473
_refine_ls_restrained_S_all 1.046
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0620P)^2^+0.3702P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1199
_refine_ls_wR_factor_ref 0.1367
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups
At 1.5 times of:
All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
C3(H3)
2.b Secondary CH2 refined with riding coordinates:
C2(H2A,H2B), C4(H4A,H4B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
C9(H9), C10(H10), C12(H12), C13(H13)
2.d Idealised Me refined as rotating group:
C14(H14A,H14B,H14C)
2.e Idealised tetrahedral OH refined as rotating group:
O1(H1)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.46053(14) 0.04698(12) 0.83419(11) 0.0634(4) Uani 1 1 d . . . . .
O1 O 0.4502(2) -0.02670(14) 0.62725(14) 0.0654(5) Uani 1 1 d . . . . .
H1 H 0.449998 -0.047600 0.559685 0.098 Uiso 1 1 calc R U . . .
O2 O 0.6091(2) 0.09702(14) 0.60013(14) 0.0720(5) Uani 1 1 d . . . . .
O3 O 0.8554(2) -0.40757(13) 0.91978(15) 0.0708(5) Uani 1 1 d . . . . .
C1 C 0.7265(2) 0.05469(18) 0.88276(18) 0.0493(5) Uani 1 1 d . . . . .
C2 C 0.7305(3) 0.1262(2) 0.9976(2) 0.0637(7) Uani 1 1 d . . . . .
H2A H 0.640398 0.122904 1.019341 0.076 Uiso 1 1 calc R U . . .
H2B H 0.819456 0.116518 1.068428 0.076 Uiso 1 1 calc R U . . .
C3 C 0.7371(3) 0.2234(2) 0.9133(2) 0.0664(7) Uani 1 1 d . . . . .
H3 H 0.778013 0.295418 0.948973 0.080 Uiso 1 1 calc R U . . .
C4 C 0.5836(3) 0.21865(19) 0.8140(2) 0.0643(7) Uani 1 1 d . . . . .
H4A H 0.581851 0.258369 0.740484 0.077 Uiso 1 1 calc R U . . .
H4B H 0.505643 0.247046 0.843013 0.077 Uiso 1 1 calc R U . . .
C5 C 0.5721(2) 0.09204(18) 0.79411(18) 0.0497(5) Uani 1 1 d . . . . .
C6 C 0.8300(3) 0.14676(19) 0.8597(2) 0.0609(6) Uani 1 1 d . . . . .
H6A H 0.934248 0.140181 0.909251 0.073 Uiso 1 1 calc R U . . .
H6B H 0.817550 0.160044 0.774112 0.073 Uiso 1 1 calc R U . . .
C7 C 0.5408(2) 0.05120(17) 0.66350(18) 0.0463(5) Uani 1 1 d . . . . .
C8 C 0.7614(2) -0.06690(18) 0.88993(17) 0.0468(5) Uani 1 1 d . . . . .
C9 C 0.8313(3) -0.11655(19) 0.81517(19) 0.0532(6) Uani 1 1 d . . . . .
H9 H 0.857242 -0.072538 0.759122 0.064 Uiso 1 1 calc R U . . .
C10 C 0.8638(3) -0.22904(19) 0.82106(19) 0.0549(6) Uani 1 1 d . . . . .
H10 H 0.910950 -0.259657 0.769657 0.066 Uiso 1 1 calc R U . . .
C11 C 0.8260(2) -0.29615(18) 0.90369(18) 0.0516(6) Uani 1 1 d . . . . .
C12 C 0.7543(2) -0.24847(19) 0.97821(19) 0.0563(6) Uani 1 1 d . . . . .
H12 H 0.727269 -0.292858 1.033384 0.068 Uiso 1 1 calc R U . . .
C13 C 0.7228(3) -0.13643(19) 0.97153(18) 0.0543(6) Uani 1 1 d . . . . .
H13 H 0.674668 -0.106232 1.022476 0.065 Uiso 1 1 calc R U . . .
C14 C 0.9141(4) -0.4629(2) 0.8373(3) 0.0821(8) Uani 1 1 d . . . . .
H14A H 0.848445 -0.451930 0.754868 0.123 Uiso 1 1 calc R U . . .
H14B H 0.922813 -0.541135 0.855627 0.123 Uiso 1 1 calc R U . . .
H14C H 1.010605 -0.432941 0.845533 0.123 Uiso 1 1 calc R U . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0518(8) 0.0887(9) 0.0550(7) -0.0096(6) 0.0247(6) -0.0029(7)
O1 0.0791(12) 0.0685(11) 0.0484(9) -0.0119(8) 0.0207(9) -0.0190(9)
O2 0.0937(13) 0.0782(11) 0.0501(9) -0.0087(8) 0.0319(9) -0.0291(10)
O3 0.0865(13) 0.0628(10) 0.0646(10) 0.0092(8) 0.0272(9) 0.0057(9)
C1 0.0482(13) 0.0615(13) 0.0393(10) -0.0090(9) 0.0158(9) -0.0013(10)
C2 0.0643(15) 0.0797(17) 0.0453(12) -0.0175(11) 0.0156(11) -0.0030(13)
C3 0.0678(16) 0.0637(15) 0.0642(15) -0.0231(12) 0.0169(12) -0.0077(12)
C4 0.0665(16) 0.0618(15) 0.0640(14) -0.0136(11) 0.0207(12) 0.0061(12)
C5 0.0485(13) 0.0580(13) 0.0450(11) -0.0082(9) 0.0186(10) -0.0027(10)
C6 0.0534(14) 0.0677(15) 0.0621(14) -0.0090(11) 0.0201(11) -0.0082(11)
C7 0.0478(12) 0.0466(11) 0.0426(11) -0.0005(9) 0.0122(9) 0.0003(10)
C8 0.0402(11) 0.0633(13) 0.0350(10) -0.0031(9) 0.0100(9) -0.0003(10)
C9 0.0598(14) 0.0630(14) 0.0429(11) 0.0039(10) 0.0252(10) 0.0030(11)
C10 0.0589(14) 0.0632(14) 0.0470(12) 0.0004(10) 0.0232(10) 0.0085(11)
C11 0.0496(13) 0.0603(14) 0.0401(11) 0.0020(9) 0.0084(10) 0.0010(10)
C12 0.0599(14) 0.0692(15) 0.0417(11) 0.0067(10) 0.0192(10) -0.0045(12)
C13 0.0541(13) 0.0726(15) 0.0399(11) -0.0041(10) 0.0206(10) -0.0007(11)
C14 0.107(2) 0.0664(16) 0.0754(17) 0.0006(13) 0.0328(17) 0.0211(15)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C5 1.398(2) . ?
O1 H1 0.8200 . ?
O1 C7 1.246(2) . ?
O2 C7 1.254(2) . ?
O3 C11 1.365(3) . ?
O3 C14 1.418(3) . ?
C1 C2 1.570(3) . ?
C1 C5 1.552(3) . ?
C1 C6 1.559(3) . ?
C1 C8 1.492(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.535(4) . ?
C3 H3 0.9800 . ?
C3 C4 1.531(3) . ?
C3 C6 1.539(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.534(3) . ?
C5 C7 1.521(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C8 C9 1.387(3) . ?
C8 C13 1.396(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.381(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.385(3) . ?
C11 C12 1.386(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.373(3) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O1 H1 109.5 . . ?
C11 O3 C14 118.31(19) . . ?
C5 C1 C2 98.90(17) . . ?
C5 C1 C6 101.21(17) . . ?
C6 C1 C2 85.26(16) . . ?
C8 C1 C2 122.95(18) . . ?
C8 C1 C5 117.57(17) . . ?
C8 C1 C6 124.12(18) . . ?
C1 C2 H2A 114.9 . . ?
C1 C2 H2B 114.9 . . ?
H2A C2 H2B 111.9 . . ?
C3 C2 C1 82.69(16) . . ?
C3 C2 H2A 114.9 . . ?
C3 C2 H2B 114.9 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C6 87.18(18) . . ?
C4 C3 C2 102.6(2) . . ?
C4 C3 H3 119.7 . . ?
C4 C3 C6 101.92(18) . . ?
C6 C3 H3 119.7 . . ?
C3 C4 H4A 112.0 . . ?
C3 C4 H4B 112.0 . . ?
C3 C4 C5 98.78(18) . . ?
H4A C4 H4B 109.7 . . ?
C5 C4 H4A 112.0 . . ?
C5 C4 H4B 112.0 . . ?
F1 C5 C1 108.91(17) . . ?
F1 C5 C4 110.91(17) . . ?
F1 C5 C7 106.49(16) . . ?
C4 C5 C1 100.47(17) . . ?
C7 C5 C1 113.26(17) . . ?
C7 C5 C4 116.66(18) . . ?
C1 C6 H6A 114.8 . . ?
C1 C6 H6B 114.8 . . ?
C3 C6 C1 82.90(17) . . ?
C3 C6 H6A 114.8 . . ?
C3 C6 H6B 114.8 . . ?
H6A C6 H6B 111.9 . . ?
O1 C7 O2 124.43(19) . . ?
O1 C7 C5 117.53(19) . . ?
O2 C7 C5 118.03(18) . . ?
C9 C8 C1 121.90(18) . . ?
C9 C8 C13 116.9(2) . . ?
C13 C8 C1 121.23(19) . . ?
C8 C9 H9 118.9 . . ?
C10 C9 C8 122.3(2) . . ?
C10 C9 H9 118.9 . . ?
C9 C10 H10 120.1 . . ?
C9 C10 C11 119.8(2) . . ?
C11 C10 H10 120.1 . . ?
O3 C11 C10 125.1(2) . . ?
O3 C11 C12 116.1(2) . . ?
C10 C11 C12 118.8(2) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.8(2) . . ?
C13 C12 H12 119.6 . . ?
C8 C13 H13 119.3 . . ?
C12 C13 C8 121.4(2) . . ?
C12 C13 H13 119.3 . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C5 C7 O1 -14.0(3) . . . . ?
F1 C5 C7 O2 166.90(19) . . . . ?
O3 C11 C12 C13 178.40(19) . . . . ?
C1 C2 C3 C4 67.02(18) . . . . ?
C1 C2 C3 C6 -34.57(16) . . . . ?
C1 C5 C7 O1 105.7(2) . . . . ?
C1 C5 C7 O2 -73.4(3) . . . . ?
C1 C8 C9 C10 -179.9(2) . . . . ?
C1 C8 C13 C12 179.83(19) . . . . ?
C2 C1 C5 F1 -70.63(19) . . . . ?
C2 C1 C5 C4 45.9(2) . . . . ?
C2 C1 C5 C7 171.08(18) . . . . ?
C2 C1 C6 C3 -34.02(17) . . . . ?
C2 C1 C8 C9 -146.1(2) . . . . ?
C2 C1 C8 C13 34.9(3) . . . . ?
C2 C3 C4 C5 -42.9(2) . . . . ?
C2 C3 C6 C1 34.82(16) . . . . ?
C3 C4 C5 F1 112.32(19) . . . . ?
C3 C4 C5 C1 -2.7(2) . . . . ?
C3 C4 C5 C7 -125.5(2) . . . . ?
C4 C3 C6 C1 -67.51(19) . . . . ?
C4 C5 C7 O1 -138.4(2) . . . . ?
C4 C5 C7 O2 42.5(3) . . . . ?
C5 C1 C2 C3 -66.48(18) . . . . ?
C5 C1 C6 C3 64.14(17) . . . . ?
C5 C1 C8 C9 90.8(2) . . . . ?
C5 C1 C8 C13 -88.3(2) . . . . ?
C6 C1 C2 C3 34.15(17) . . . . ?
C6 C1 C5 F1 -157.53(16) . . . . ?
C6 C1 C5 C4 -41.0(2) . . . . ?
C6 C1 C5 C7 84.2(2) . . . . ?
C6 C1 C8 C9 -37.4(3) . . . . ?
C6 C1 C8 C13 143.5(2) . . . . ?
C6 C3 C4 C5 46.8(2) . . . . ?
C8 C1 C2 C3 162.3(2) . . . . ?
C8 C1 C5 F1 64.0(2) . . . . ?
C8 C1 C5 C4 -179.44(18) . . . . ?
C8 C1 C5 C7 -54.3(2) . . . . ?
C8 C1 C6 C3 -161.11(19) . . . . ?
C8 C9 C10 C11 0.1(3) . . . . ?
C9 C8 C13 C12 0.7(3) . . . . ?
C9 C10 C11 O3 -178.4(2) . . . . ?
C9 C10 C11 C12 0.7(3) . . . . ?
C10 C11 C12 C13 -0.8(3) . . . . ?
C11 C12 C13 C8 0.0(3) . . . . ?
C13 C8 C9 C10 -0.8(3) . . . . ?
C14 O3 C11 C10 -7.5(3) . . . . ?
C14 O3 C11 C12 173.4(2) . . . . ?
_shelx_res_file
;
TITL vd29 in P21/c #14
vd29.res
created by SHELXL-2016/6 at 19:47:21 on 02-Sep-2022
REM reset to P21/c #14
CELL 0.71073 9.5011 11.9938 11.5637 90 109.2895 90
ZERR 4 0.0014 0.0015 0.0017 0 0.0074 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H F O
UNIT 56 60 4 12
L.S. 4 0 0
PLAN 5
SIZE 0.2 0.18 0.17
TEMP 23
CONF
BOND
MORE -1
BOND $H
fmap 2 53
acta
OMIT -2 50
REM
REM
REM
WGHT 0.062000 0.370200
FVAR 0.17522
F1 3 0.460530 0.046980 0.834185 11.00000 0.05177 0.08875 =
0.05501 -0.00964 0.02472 -0.00289
O1 4 0.450163 -0.026701 0.627247 11.00000 0.07906 0.06855 =
0.04841 -0.01186 0.02074 -0.01897
AFIX 147
H1 2 0.449998 -0.047600 0.559685 11.00000 -1.50000
AFIX 0
O2 4 0.609061 0.097017 0.600131 11.00000 0.09374 0.07815 =
0.05014 -0.00871 0.03195 -0.02908
O3 4 0.855394 -0.407566 0.919784 11.00000 0.08653 0.06277 =
0.06463 0.00919 0.02718 0.00570
C1 1 0.726504 0.054689 0.882765 11.00000 0.04817 0.06154 =
0.03928 -0.00901 0.01584 -0.00135
C2 1 0.730549 0.126168 0.997581 11.00000 0.06426 0.07974 =
0.04531 -0.01752 0.01559 -0.00303
AFIX 23
H2A 2 0.640398 0.122904 1.019341 11.00000 -1.20000
H2B 2 0.819456 0.116518 1.068428 11.00000 -1.20000
AFIX 0
C3 1 0.737145 0.223443 0.913287 11.00000 0.06777 0.06369 =
0.06423 -0.02310 0.01692 -0.00767
AFIX 13
H3 2 0.778013 0.295418 0.948973 11.00000 -1.20000
AFIX 0
C4 1 0.583579 0.218647 0.814009 11.00000 0.06645 0.06181 =
0.06403 -0.01358 0.02068 0.00609
AFIX 23
H4A 2 0.581851 0.258369 0.740484 11.00000 -1.20000
H4B 2 0.505643 0.247046 0.843013 11.00000 -1.20000
AFIX 0
C5 1 0.572097 0.092036 0.794105 11.00000 0.04852 0.05799 =
0.04500 -0.00818 0.01857 -0.00266
C6 1 0.829993 0.146764 0.859670 11.00000 0.05342 0.06774 =
0.06213 -0.00903 0.02006 -0.00817
AFIX 23
H6A 2 0.934248 0.140181 0.909251 11.00000 -1.20000
H6B 2 0.817550 0.160044 0.774112 11.00000 -1.20000
AFIX 0
C7 1 0.540828 0.051196 0.663500 11.00000 0.04784 0.04662 =
0.04256 -0.00051 0.01224 0.00034
C8 1 0.761358 -0.066896 0.889927 11.00000 0.04021 0.06333 =
0.03500 -0.00314 0.00995 -0.00027
C9 1 0.831307 -0.116545 0.815171 11.00000 0.05982 0.06296 =
0.04293 0.00394 0.02520 0.00304
AFIX 43
H9 2 0.857242 -0.072538 0.759122 11.00000 -1.20000
AFIX 0
C10 1 0.863786 -0.229043 0.821058 11.00000 0.05891 0.06319 =
0.04698 0.00039 0.02320 0.00852
AFIX 43
H10 2 0.910950 -0.259657 0.769657 11.00000 -1.20000
AFIX 0
C11 1 0.825950 -0.296147 0.903687 11.00000 0.04961 0.06027 =
0.04013 0.00201 0.00836 0.00101
C12 1 0.754308 -0.248466 0.978206 11.00000 0.05987 0.06917 =
0.04172 0.00668 0.01919 -0.00449
AFIX 43
H12 2 0.727269 -0.292858 1.033384 11.00000 -1.20000
AFIX 0
C13 1 0.722768 -0.136431 0.971535 11.00000 0.05409 0.07259 =
0.03990 -0.00414 0.02059 -0.00066
AFIX 43
H13 2 0.674668 -0.106232 1.022476 11.00000 -1.20000
AFIX 0
C14 1 0.914054 -0.462860 0.837288 11.00000 0.10651 0.06642 =
0.07542 0.00060 0.03279 0.02108
AFIX 137
H14A 2 0.848445 -0.451930 0.754868 11.00000 -1.50000
H14B 2 0.922813 -0.541135 0.855627 11.00000 -1.50000
H14C 2 1.010605 -0.432941 0.845533 11.00000 -1.50000
AFIX 0
HKLF 4
REM vd29 in P21/c #14
REM R1 = 0.0473 for 1595 Fo > 4sig(Fo) and 0.0675 for all 2190 data
REM 165 parameters refined using 0 restraints
END
WGHT 0.0620 0.3695
REM Highest difference peak 0.177, deepest hole -0.235, 1-sigma level 0.040
Q1 1 0.6270 0.1142 0.6044 11.00000 0.05 0.18
Q2 1 0.7452 -0.0021 0.8807 11.00000 0.05 0.17
Q3 1 0.6059 0.0586 0.5316 11.00000 0.05 0.17
Q4 1 0.8436 -0.0815 0.8868 11.00000 0.05 0.17
Q5 1 0.6697 0.0744 0.8248 11.00000 0.05 0.16
;
_shelx_res_checksum 73036
_olex2_submission_special_instructions 'No special instructions were received'
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_v107
_audit_block_doi 10.5517/ccdc.csd.cc2gr9yh
_database_code_depnum_ccdc_archive 'CCDC 2286527'
loop_
_citation_id
_citation_doi
_citation_year
1 10.26434/chemrxiv-2023-78z7p 2023
loop_
_audit_author_name
_audit_author_address
'Iryna Sadkova'
;Enamine Ltd
Ukraine
;
_audit_update_record
;
2023-08-03 deposited with the CCDC. 2023-10-27 downloaded from the CCDC.
;
_audit_creation_date 2023-03-07
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number 2016/6
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C18 H17 Cl2 F2 N3 O'
_chemical_formula_sum 'C18 H17 Cl2 F2 N3 O'
_chemical_formula_weight 400.24
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system monoclinic
_space_group_IT_number 14
_space_group_name_H-M_alt 'P 1 21/c 1'
_space_group_name_Hall '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a 10.9193(6)
_cell_length_b 18.5629(12)
_cell_length_c 9.7993(5)
_cell_angle_alpha 90
_cell_angle_beta 115.272(3)
_cell_angle_gamma 90
_cell_volume 1796.16(18)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 5641
_cell_measurement_temperature 273.15
_cell_measurement_theta_max 24.69
_cell_measurement_theta_min 2.19
_shelx_estimated_absorpt_T_max 0.984
_shelx_estimated_absorpt_T_min 0.911
_exptl_absorpt_coefficient_mu 0.394
_exptl_absorpt_correction_T_max ?
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_type none
_exptl_absorpt_process_details ?
_exptl_absorpt_special_details ?
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.480
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description plate
_exptl_crystal_F_000 824
_exptl_crystal_size_max 0.24
_exptl_crystal_size_mid 0.17
_exptl_crystal_size_min 0.04
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0508
_diffrn_reflns_av_unetI/netI 0.0309
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max 12
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_k_max 22
_diffrn_reflns_limit_k_min -21
_diffrn_reflns_limit_l_max 11
_diffrn_reflns_limit_l_min -11
_diffrn_reflns_number 26745
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full 24.998
_diffrn_reflns_theta_max 24.998
_diffrn_reflns_theta_min 2.062
_diffrn_ambient_temperature 273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type 'Bruker APEX-II CCD'
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source ?
_diffrn_source_current 30.0
_diffrn_source_power 1.2
_diffrn_source_voltage 40.0
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 2531
_reflns_number_total 3158
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement ?
_computing_data_collection ?
_computing_data_reduction ?
_computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement 'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max 0.260
_refine_diff_density_min -0.233
_refine_diff_density_rms 0.052
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.059
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 240
_refine_ls_number_reflns 3158
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0535
_refine_ls_R_factor_gt 0.0404
_refine_ls_restrained_S_all 1.059
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0482P)^2^+1.0152P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0969
_refine_ls_wR_factor_ref 0.1041
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups
At 1.5 times of:
All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
C1(H1A), C3(H3), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
C2(H2A,H2B), C4(H4A,H4B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
C8(H8), C11(H11), C12(H12), C15(H15)
2.d Idealised Me refined as rotating group:
C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens mixed
_atom_sites_solution_primary dual
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.62468(7) 0.59194(3) 0.48773(7) 0.03961(19) Uani 1 1 d . . . . .
Cl2 Cl 0.89394(6) 0.57636(3) 0.44677(8) 0.0428(2) Uani 1 1 d . . . . .
F1 F 0.94229(17) 0.28680(9) 0.63398(18) 0.0588(5) Uani 1 1 d . . . . .
F2 F 1.01885(17) 0.18708(10) 0.75668(17) 0.0693(6) Uani 1 1 d . . . . .
O1 O 0.61921(15) 0.27065(9) 0.47992(16) 0.0298(4) Uani 1 1 d . . . . .
N1 N 0.53163(18) 0.26086(10) 0.2247(2) 0.0245(4) Uani 1 1 d . . . . .
H1 H 0.545(2) 0.2437(13) 0.154(3) 0.026(7) Uiso 1 1 d . . . . .
N2 N 0.92212(18) 0.12538(11) 0.4873(2) 0.0303(5) Uani 1 1 d . . . . .
N3 N 0.84598(18) 0.10379(10) 0.3432(2) 0.0273(4) Uani 1 1 d . . . . .
C1 C 0.4150(2) 0.30705(12) 0.1939(3) 0.0261(5) Uani 1 1 d . . . . .
H1A H 0.405901 0.316431 0.289615 0.031 Uiso 1 1 calc R U . . .
C2 C 0.2786(2) 0.27743(13) 0.0719(3) 0.0392(6) Uani 1 1 d . . . . .
H2A H 0.291574 0.232434 0.025388 0.047 Uiso 1 1 calc R U . . .
H2B H 0.211340 0.269270 0.113157 0.047 Uiso 1 1 calc R U . . .
C3 C 0.2394(2) 0.34027(14) -0.0381(3) 0.0398(6) Uani 1 1 d . . . . .
H3 H 0.152465 0.338602 -0.131782 0.048 Uiso 1 1 calc R U . . .
C4 C 0.2712(2) 0.40576(13) 0.0683(3) 0.0335(6) Uani 1 1 d . . . . .
H4A H 0.237401 0.402027 0.147046 0.040 Uiso 1 1 calc R U . . .
H4B H 0.249996 0.453132 0.016994 0.040 Uiso 1 1 calc R U . . .
C5 C 0.4197(2) 0.37972(12) 0.1178(2) 0.0263(5) Uani 1 1 d . . . . .
C6 C 0.3734(2) 0.35690(14) -0.0495(3) 0.0373(6) Uani 1 1 d . . . . .
H6A H 0.368197 0.396662 -0.119157 0.045 Uiso 1 1 calc R U . . .
H6B H 0.420636 0.314237 -0.064694 0.045 Uiso 1 1 calc R U . . .
C7 C 0.5389(2) 0.42752(12) 0.1993(2) 0.0258(5) Uani 1 1 d . . . . .
C8 C 0.5308(2) 0.48138(12) 0.2932(2) 0.0268(5) Uani 1 1 d . . . . .
H8 H 0.449010 0.488081 0.303731 0.032 Uiso 1 1 calc R U . . .
C9 C 0.6408(2) 0.52545(12) 0.3716(2) 0.0271(5) Uani 1 1 d . . . . .
C10 C 0.7604(2) 0.51740(12) 0.3568(3) 0.0297(5) Uani 1 1 d . . . . .
C11 C 0.7704(2) 0.46360(13) 0.2642(3) 0.0336(6) Uani 1 1 d . . . . .
H11 H 0.852483 0.457123 0.254193 0.040 Uiso 1 1 calc R U . . .
C12 C 0.6603(2) 0.41911(13) 0.1858(3) 0.0324(6) Uani 1 1 d . . . . .
H12 H 0.667700 0.382429 0.122162 0.039 Uiso 1 1 calc R U . . .
C13 C 0.6235(2) 0.24505(11) 0.3649(2) 0.0223(5) Uani 1 1 d . . . . .
C14 C 0.7303(2) 0.19254(11) 0.3788(2) 0.0224(5) Uani 1 1 d . . . . .
C15 C 0.7323(2) 0.14248(12) 0.2757(2) 0.0248(5) Uani 1 1 d . . . . .
H15 H 0.665323 0.136545 0.175141 0.030 Uiso 1 1 calc R U . . .
C16 C 0.8519(2) 0.17909(12) 0.5084(2) 0.0262(5) Uani 1 1 d . . . . .
C17 C 0.9059(2) 0.21927(14) 0.6548(3) 0.0373(6) Uani 1 1 d . . . . .
H17 H 0.835536 0.221608 0.694596 0.045 Uiso 1 1 calc R U . . .
C18 C 0.8963(3) 0.04709(13) 0.2776(3) 0.0365(6) Uani 1 1 d . . . . .
H18A H 0.971743 0.065717 0.258796 0.055 Uiso 1 1 calc R U . . .
H18B H 0.823421 0.031114 0.182159 0.055 Uiso 1 1 calc R U . . .
H18C H 0.927724 0.006334 0.347625 0.055 Uiso 1 1 calc R U . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0492(4) 0.0303(3) 0.0440(4) -0.0091(3) 0.0243(3) -0.0056(3)
Cl2 0.0316(3) 0.0396(4) 0.0509(4) -0.0039(3) 0.0116(3) -0.0079(3)
F1 0.0632(11) 0.0504(10) 0.0524(10) -0.0179(8) 0.0148(8) -0.0225(9)
F2 0.0579(11) 0.0838(13) 0.0326(9) -0.0099(8) -0.0128(8) 0.0241(10)
O1 0.0301(9) 0.0402(10) 0.0206(8) -0.0044(7) 0.0124(7) -0.0007(7)
N1 0.0278(10) 0.0257(10) 0.0197(10) -0.0012(8) 0.0097(8) 0.0056(8)
N2 0.0238(10) 0.0351(11) 0.0270(11) 0.0002(8) 0.0058(8) 0.0016(9)
N3 0.0249(10) 0.0286(11) 0.0274(10) -0.0005(8) 0.0103(8) 0.0022(8)
C1 0.0244(12) 0.0262(12) 0.0277(12) -0.0011(9) 0.0110(9) 0.0034(9)
C2 0.0275(13) 0.0311(14) 0.0486(16) -0.0092(11) 0.0061(11) 0.0010(11)
C3 0.0271(13) 0.0415(15) 0.0345(14) -0.0086(11) -0.0025(11) 0.0082(11)
C4 0.0270(13) 0.0304(13) 0.0365(14) -0.0022(10) 0.0071(11) 0.0064(10)
C5 0.0252(12) 0.0257(12) 0.0251(12) -0.0007(9) 0.0079(9) 0.0052(9)
C6 0.0395(14) 0.0432(15) 0.0209(12) 0.0015(10) 0.0047(11) 0.0139(12)
C7 0.0267(12) 0.0235(12) 0.0252(12) 0.0053(9) 0.0092(9) 0.0050(9)
C8 0.0282(12) 0.0250(12) 0.0292(12) 0.0035(9) 0.0143(10) 0.0029(10)
C9 0.0357(13) 0.0196(12) 0.0275(12) 0.0034(9) 0.0150(10) 0.0010(10)
C10 0.0263(12) 0.0274(13) 0.0308(13) 0.0059(10) 0.0077(10) -0.0012(10)
C11 0.0258(12) 0.0386(15) 0.0368(14) 0.0019(11) 0.0137(11) 0.0046(11)
C12 0.0316(13) 0.0325(14) 0.0324(13) -0.0012(10) 0.0129(11) 0.0045(10)
C13 0.0234(11) 0.0213(11) 0.0227(12) 0.0006(9) 0.0102(9) -0.0043(9)
C14 0.0226(11) 0.0240(12) 0.0197(11) 0.0019(9) 0.0082(9) -0.0037(9)
C15 0.0236(11) 0.0271(12) 0.0220(11) 0.0029(9) 0.0082(9) 0.0004(9)
C16 0.0246(11) 0.0288(13) 0.0241(12) 0.0021(9) 0.0092(10) -0.0030(10)
C17 0.0293(13) 0.0424(16) 0.0293(13) -0.0012(11) 0.0022(11) 0.0002(11)
C18 0.0355(14) 0.0326(14) 0.0431(15) -0.0045(11) 0.0184(12) 0.0039(11)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C9 1.738(2) . ?
Cl2 C10 1.733(2) . ?
F1 C17 1.357(3) . ?
F2 C17 1.351(3) . ?
O1 C13 1.242(2) . ?
N1 H1 0.83(2) . ?
N1 C1 1.456(3) . ?
N1 C13 1.343(3) . ?
N2 N3 1.358(3) . ?
N2 C16 1.327(3) . ?
N3 C15 1.339(3) . ?
N3 C18 1.458(3) . ?
C1 H1A 1.0000 . ?
C1 C2 1.558(3) . ?
C1 C5 1.553(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.521(4) . ?
C3 H3 1.0000 . ?
C3 C4 1.542(3) . ?
C3 C6 1.546(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.557(3) . ?
C5 C6 1.554(3) . ?
C5 C7 1.494(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.387(3) . ?
C7 C12 1.396(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.384(3) . ?
C9 C10 1.382(3) . ?
C10 C11 1.385(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.389(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.482(3) . ?
C14 C15 1.380(3) . ?
C14 C16 1.413(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.496(3) . ?
C17 H17 1.0000 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 H1 120.1(16) . . ?
C13 N1 H1 116.8(16) . . ?
C13 N1 C1 123.11(19) . . ?
C16 N2 N3 104.24(17) . . ?
N2 N3 C18 119.54(18) . . ?
C15 N3 N2 112.47(18) . . ?
C15 N3 C18 127.88(19) . . ?
N1 C1 H1A 109.6 . . ?
N1 C1 C2 114.59(18) . . ?
N1 C1 C5 113.96(18) . . ?
C2 C1 H1A 109.6 . . ?
C5 C1 H1A 109.6 . . ?
C5 C1 C2 98.90(18) . . ?
C1 C2 H2A 111.9 . . ?
C1 C2 H2B 111.9 . . ?
H2A C2 H2B 109.6 . . ?
C3 C2 C1 99.26(19) . . ?
C3 C2 H2A 111.9 . . ?
C3 C2 H2B 111.9 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 102.2(2) . . ?
C2 C3 C6 102.44(19) . . ?
C4 C3 H3 119.8 . . ?
C4 C3 C6 86.81(19) . . ?
C6 C3 H3 119.8 . . ?
C3 C4 H4A 114.9 . . ?
C3 C4 H4B 114.9 . . ?
C3 C4 C5 82.53(17) . . ?
H4A C4 H4B 111.9 . . ?
C5 C4 H4A 114.9 . . ?
C5 C4 H4B 114.9 . . ?
C1 C5 C4 100.13(18) . . ?
C1 C5 C6 101.96(18) . . ?
C6 C5 C4 85.99(17) . . ?
C7 C5 C1 117.33(18) . . ?
C7 C5 C4 122.38(19) . . ?
C7 C5 C6 122.8(2) . . ?
C3 C6 C5 82.49(17) . . ?
C3 C6 H6A 114.9 . . ?
C3 C6 H6B 114.9 . . ?
C5 C6 H6A 114.9 . . ?
C5 C6 H6B 114.9 . . ?
H6A C6 H6B 111.9 . . ?
C8 C7 C5 119.7(2) . . ?
C8 C7 C12 118.4(2) . . ?
C12 C7 C5 121.9(2) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 C7 120.6(2) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 Cl1 118.48(18) . . ?
C10 C9 Cl1 120.65(18) . . ?
C10 C9 C8 120.9(2) . . ?
C9 C10 Cl2 120.38(18) . . ?
C9 C10 C11 119.3(2) . . ?
C11 C10 Cl2 120.30(18) . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 120.0(2) . . ?
C12 C11 H11 120.0 . . ?
C7 C12 H12 119.5 . . ?
C11 C12 C7 120.9(2) . . ?
C11 C12 H12 119.5 . . ?
O1 C13 N1 122.9(2) . . ?
O1 C13 C14 120.12(18) . . ?
N1 C13 C14 116.90(18) . . ?
C15 C14 C13 129.36(19) . . ?
C15 C14 C16 103.71(19) . . ?
C16 C14 C13 126.80(19) . . ?
N3 C15 C14 107.49(19) . . ?
N3 C15 H15 126.3 . . ?
C14 C15 H15 126.3 . . ?
N2 C16 C14 112.09(19) . . ?
N2 C16 C17 120.43(19) . . ?
C14 C16 C17 127.4(2) . . ?
F1 C17 C16 109.7(2) . . ?
F1 C17 H17 110.0 . . ?
F2 C17 F1 106.6(2) . . ?
F2 C17 C16 110.5(2) . . ?
F2 C17 H17 110.0 . . ?
C16 C17 H17 110.0 . . ?
N3 C18 H18A 109.5 . . ?
N3 C18 H18B 109.5 . . ?
N3 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C9 C10 Cl2 -3.2(3) . . . . ?
Cl1 C9 C10 C11 179.59(17) . . . . ?
Cl2 C10 C11 C12 -176.39(18) . . . . ?
O1 C13 C14 C15 158.5(2) . . . . ?
O1 C13 C14 C16 -16.5(3) . . . . ?
N1 C1 C2 C3 -123.0(2) . . . . ?
N1 C1 C5 C4 167.42(18) . . . . ?
N1 C1 C5 C6 79.4(2) . . . . ?
N1 C1 C5 C7 -57.8(3) . . . . ?
N1 C13 C14 C15 -19.3(3) . . . . ?
N1 C13 C14 C16 165.6(2) . . . . ?
N2 N3 C15 C14 -0.4(3) . . . . ?
N2 C16 C17 F1 109.7(2) . . . . ?
N2 C16 C17 F2 -7.6(3) . . . . ?
N3 N2 C16 C14 0.0(2) . . . . ?
N3 N2 C16 C17 -178.0(2) . . . . ?
C1 N1 C13 O1 -2.7(3) . . . . ?
C1 N1 C13 C14 175.08(18) . . . . ?
C1 C2 C3 C4 -43.7(2) . . . . ?
C1 C2 C3 C6 45.6(2) . . . . ?
C1 C5 C6 C3 65.16(19) . . . . ?
C1 C5 C7 C8 -94.1(2) . . . . ?
C1 C5 C7 C12 84.9(3) . . . . ?
C2 C1 C5 C4 45.4(2) . . . . ?
C2 C1 C5 C6 -42.6(2) . . . . ?
C2 C1 C5 C7 -179.81(19) . . . . ?
C2 C3 C4 C5 67.4(2) . . . . ?
C2 C3 C6 C5 -67.09(19) . . . . ?
C3 C4 C5 C1 -66.99(19) . . . . ?
C3 C4 C5 C6 34.46(18) . . . . ?
C3 C4 C5 C7 161.3(2) . . . . ?
C4 C3 C6 C5 34.72(17) . . . . ?
C4 C5 C6 C3 -34.36(17) . . . . ?
C4 C5 C7 C8 30.1(3) . . . . ?
C4 C5 C7 C12 -150.9(2) . . . . ?
C5 C1 C2 C3 -1.4(2) . . . . ?
C5 C7 C8 C9 178.9(2) . . . . ?
C5 C7 C12 C11 -179.2(2) . . . . ?
C6 C3 C4 C5 -34.63(17) . . . . ?
C6 C5 C7 C8 138.2(2) . . . . ?
C6 C5 C7 C12 -42.8(3) . . . . ?
C7 C5 C6 C3 -160.8(2) . . . . ?
C7 C8 C9 Cl1 -179.93(16) . . . . ?
C7 C8 C9 C10 0.8(3) . . . . ?
C8 C7 C12 C11 -0.1(3) . . . . ?
C8 C9 C10 Cl2 176.11(17) . . . . ?
C8 C9 C10 C11 -1.1(3) . . . . ?
C9 C10 C11 C12 0.9(3) . . . . ?
C10 C11 C12 C7 -0.2(4) . . . . ?
C12 C7 C8 C9 -0.1(3) . . . . ?
C13 N1 C1 C2 -134.3(2) . . . . ?
C13 N1 C1 C5 112.8(2) . . . . ?
C13 C14 C15 N3 -175.5(2) . . . . ?
C13 C14 C16 N2 175.8(2) . . . . ?
C13 C14 C16 C17 -6.4(4) . . . . ?
C14 C16 C17 F1 -68.0(3) . . . . ?
C14 C16 C17 F2 174.8(2) . . . . ?
C15 C14 C16 N2 -0.2(2) . . . . ?
C15 C14 C16 C17 177.6(2) . . . . ?
C16 N2 N3 C15 0.2(2) . . . . ?
C16 N2 N3 C18 176.8(2) . . . . ?
C16 C14 C15 N3 0.4(2) . . . . ?
C18 N3 C15 C14 -176.6(2) . . . . ?
_shelx_res_file
;
TITL v107_a.res in P2(1)/c
v107.res
created by SHELXL-2016/6 at 19:22:23 on 07-Mar-2023
REM Old TITL v107 in P2(1)/c
REM SHELXT solution in P2(1)/c
REM R1 0.145, Rweak 0.010, Alpha 0.024, Orientation as input
REM Formula found by SHELXT: C18 N3 O3 Cl2
CELL 0.71073 10.9193 18.5629 9.7993 90 115.272 90
ZERR 4 0.0006 0.0012 0.0005 0 0.003 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H Cl F N O
UNIT 72 68 8 8 12 4
L.S. 4
PLAN 5
SIZE 0.24 0.17 0.04
TEMP -100.5
CONF
BOND $H
list 4
MORE -1
fmap 2
acta
OMIT -2 50
REM
REM
REM
WGHT 0.048200 1.015200
FVAR 0.51069
CL1 3 0.624683 0.591945 0.487728 11.00000 0.04917 0.03026 =
0.04396 -0.00906 0.02426 -0.00564
CL2 3 0.893939 0.576363 0.446766 11.00000 0.03158 0.03962 =
0.05086 -0.00390 0.01161 -0.00790
F1 4 0.942285 0.286804 0.633985 11.00000 0.06317 0.05037 =
0.05240 -0.01790 0.01480 -0.02246
F2 4 1.018845 0.187080 0.756678 11.00000 0.05794 0.08384 =
0.03261 -0.00987 -0.01283 0.02411
O1 6 0.619208 0.270648 0.479917 11.00000 0.03014 0.04016 =
0.02062 -0.00444 0.01241 -0.00070
N1 5 0.531627 0.260864 0.224721 11.00000 0.02776 0.02569 =
0.01966 -0.00122 0.00971 0.00557
H1 2 0.544633 0.243686 0.154175 11.00000 0.02605
N2 5 0.922115 0.125384 0.487280 11.00000 0.02377 0.03510 =
0.02696 0.00021 0.00585 0.00157
N3 5 0.845985 0.103788 0.343158 11.00000 0.02493 0.02858 =
0.02742 -0.00048 0.01030 0.00224
C1 1 0.414989 0.307050 0.193867 11.00000 0.02439 0.02623 =
0.02771 -0.00112 0.01102 0.00336
AFIX 13
H1A 2 0.405901 0.316431 0.289615 11.00000 -1.20000
AFIX 0
C2 1 0.278627 0.277427 0.071881 11.00000 0.02748 0.03105 =
0.04860 -0.00918 0.00608 0.00097
AFIX 23
H2A 2 0.291574 0.232434 0.025388 11.00000 -1.20000
H2B 2 0.211340 0.269270 0.113157 11.00000 -1.20000
AFIX 0
C3 1 0.239372 0.340267 -0.038142 11.00000 0.02705 0.04148 =
0.03450 -0.00863 -0.00246 0.00825
AFIX 13
H3 2 0.152465 0.338602 -0.131782 11.00000 -1.20000
AFIX 0
C4 1 0.271217 0.405763 0.068288 11.00000 0.02702 0.03037 =
0.03646 -0.00215 0.00707 0.00642
AFIX 23
H4A 2 0.237401 0.402027 0.147046 11.00000 -1.20000
H4B 2 0.249996 0.453132 0.016994 11.00000 -1.20000
AFIX 0
C5 1 0.419674 0.379723 0.117765 11.00000 0.02522 0.02571 =
0.02510 -0.00073 0.00790 0.00523
C6 1 0.373432 0.356897 -0.049549 11.00000 0.03946 0.04317 =
0.02090 0.00151 0.00474 0.01388
AFIX 23
H6A 2 0.368197 0.396662 -0.119157 11.00000 -1.20000
H6B 2 0.420636 0.314237 -0.064694 11.00000 -1.20000
AFIX 0
C7 1 0.538869 0.427524 0.199260 11.00000 0.02668 0.02348 =
0.02521 0.00531 0.00920 0.00498
C8 1 0.530788 0.481382 0.293164 11.00000 0.02824 0.02501 =
0.02925 0.00352 0.01427 0.00292
AFIX 43
H8 2 0.449010 0.488081 0.303731 11.00000 -1.20000
AFIX 0
C9 1 0.640824 0.525450 0.371606 11.00000 0.03573 0.01960 =
0.02748 0.00338 0.01504 0.00096
C10 1 0.760435 0.517400 0.356821 11.00000 0.02631 0.02737 =
0.03079 0.00591 0.00766 -0.00125
C11 1 0.770378 0.463596 0.264159 11.00000 0.02578 0.03864 =
0.03685 0.00195 0.01370 0.00458
AFIX 43
H11 2 0.852483 0.457123 0.254193 11.00000 -1.20000
AFIX 0
C12 1 0.660280 0.419112 0.185817 11.00000 0.03155 0.03249 =
0.03242 -0.00122 0.01286 0.00449
AFIX 43
H12 2 0.667700 0.382429 0.122162 11.00000 -1.20000
AFIX 0
C13 1 0.623475 0.245050 0.364938 11.00000 0.02338 0.02130 =
0.02270 0.00063 0.01018 -0.00432
C14 1 0.730347 0.192536 0.378778 11.00000 0.02259 0.02402 =
0.01966 0.00192 0.00824 -0.00374
C15 1 0.732344 0.142475 0.275664 11.00000 0.02360 0.02705 =
0.02197 0.00290 0.00816 0.00040
AFIX 43
H15 2 0.665323 0.136545 0.175141 11.00000 -1.20000
AFIX 0
C16 1 0.851858 0.179088 0.508398 11.00000 0.02465 0.02880 =
0.02408 0.00207 0.00923 -0.00296
C17 1 0.905864 0.219272 0.654757 11.00000 0.02929 0.04244 =
0.02929 -0.00117 0.00218 0.00021
AFIX 13
H17 2 0.835536 0.221608 0.694596 11.00000 -1.20000
AFIX 0
C18 1 0.896344 0.047093 0.277560 11.00000 0.03547 0.03262 =
0.04314 -0.00452 0.01837 0.00393
AFIX 137
H18A 2 0.971743 0.065717 0.258796 11.00000 -1.50000
H18B 2 0.823421 0.031114 0.182159 11.00000 -1.50000
H18C 2 0.927724 0.006334 0.347625 11.00000 -1.50000
AFIX 0
HKLF 4
REM v107_a.res in P2(1)/c
REM R1 = 0.0404 for 2531 Fo > 4sig(Fo) and 0.0535 for all 3158 data
REM 240 parameters refined using 0 restraints
END
WGHT 0.0482 1.0134
REM Highest difference peak 0.260, deepest hole -0.233, 1-sigma level 0.052
Q1 1 0.8787 0.0588 0.1583 11.00000 0.05 0.26
Q2 1 0.8468 0.0105 0.2601 11.00000 0.05 0.23
Q3 1 0.4240 0.3441 0.1556 11.00000 0.05 0.23
Q4 1 0.7960 0.1966 0.4420 11.00000 0.05 0.23
Q5 1 0.9004 0.2037 0.7572 11.00000 0.05 0.22
;
_shelx_res_checksum 77834
_olex2_submission_special_instructions 'No special instructions were received'
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_v75
_audit_block_doi 10.5517/ccdc.csd.cc2gr9xg
_database_code_depnum_ccdc_archive 'CCDC 2286526'
loop_
_citation_id
_citation_doi
_citation_year
1 10.26434/chemrxiv-2023-78z7p 2023
loop_
_audit_author_name
_audit_author_address
'Iryna Sadkova'
;Enamine Ltd
Ukraine
;
_audit_update_record
;
2023-08-03 deposited with the CCDC. 2023-10-27 downloaded from the CCDC.
;
_audit_creation_date 2022-12-12
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number 2016/6
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C13 H13 F O2'
_chemical_formula_sum 'C13 H13 F O2'
_chemical_formula_weight 220.23
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system monoclinic
_space_group_IT_number 14
_space_group_name_H-M_alt 'P 1 21/n 1'
_space_group_name_Hall '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
_cell_length_a 12.2300(9)
_cell_length_b 6.3052(5)
_cell_length_c 14.0798(10)
_cell_angle_alpha 90
_cell_angle_beta 90.886(5)
_cell_angle_gamma 90
_cell_volume 1085.60(14)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 1457
_cell_measurement_temperature 273.15
_cell_measurement_theta_max 19.03
_cell_measurement_theta_min 2.19
_shelx_estimated_absorpt_T_max 0.995
_shelx_estimated_absorpt_T_min 0.985
_exptl_absorpt_coefficient_mu 0.101
_exptl_absorpt_correction_T_max ?
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_type none
_exptl_absorpt_process_details ?
_exptl_absorpt_special_details ?
_exptl_crystal_colour 'light yellow'
_exptl_crystal_colour_modifier light
_exptl_crystal_colour_primary yellow
_exptl_crystal_density_diffrn 1.347
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description plate
_exptl_crystal_F_000 464
_exptl_crystal_size_max 0.15
_exptl_crystal_size_mid 0.12
_exptl_crystal_size_min 0.05
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0709
_diffrn_reflns_av_unetI/netI 0.0487
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max 14
_diffrn_reflns_limit_h_min -14
_diffrn_reflns_limit_k_max 7
_diffrn_reflns_limit_k_min -7
_diffrn_reflns_limit_l_max 16
_diffrn_reflns_limit_l_min -16
_diffrn_reflns_number 15155
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full 24.999
_diffrn_reflns_theta_max 24.999
_diffrn_reflns_theta_min 2.189
_diffrn_ambient_temperature 273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type 'Bruker APEX-II CCD'
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source ?
_diffrn_source_current 30.0
_diffrn_source_power 1.2
_diffrn_source_voltage 40.0
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 1207
_reflns_number_total 1917
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement ?
_computing_data_collection ?
_computing_data_reduction ?
_computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement 'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max 0.146
_refine_diff_density_min -0.173
_refine_diff_density_rms 0.033
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.019
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 146
_refine_ls_number_reflns 1917
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0897
_refine_ls_R_factor_gt 0.0479
_refine_ls_restrained_S_all 1.019
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0347P)^2^+0.2835P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0918
_refine_ls_wR_factor_ref 0.1066
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups
At 1.5 times of:
All O(H) groups
2.a Ternary CH refined with riding coordinates:
C1(H1), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
C9(H9), C10(H10), C12(H12), C13(H13)
2.d Idealised tetrahedral OH refined as rotating group:
O2(H2)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary dual
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.92187(12) 0.7695(3) 0.15110(10) 0.0867(6) Uani 1 1 d . . . . .
O1 O 0.61347(12) 0.9519(3) 0.56672(11) 0.0562(5) Uani 1 1 d . . . . .
O2 O 0.54345(13) 0.7513(3) 0.45098(11) 0.0556(5) Uani 1 1 d . . . . .
H2 H 0.502562 0.853674 0.444966 0.083 Uiso 1 1 calc R U . . .
C1 C 0.67853(17) 0.5933(3) 0.54911(14) 0.0402(6) Uani 1 1 d . . . . .
H1 H 0.649666 0.467096 0.516740 0.048 Uiso 1 1 calc R U . . .
C2 C 0.80283(16) 0.6171(3) 0.52836(14) 0.0383(5) Uani 1 1 d . . . . .
C3 C 0.8474(2) 0.4219(4) 0.58426(16) 0.0560(7) Uani 1 1 d . . . . .
H3A H 0.807080 0.291364 0.573597 0.067 Uiso 1 1 calc R U . . .
H3B H 0.925734 0.400483 0.580318 0.067 Uiso 1 1 calc R U . . .
C4 C 0.8104(2) 0.5528(4) 0.67127(16) 0.0567(7) Uani 1 1 d . . . . .
H4 H 0.843118 0.525714 0.734085 0.068 Uiso 1 1 calc R U . . .
C5 C 0.68715(19) 0.5508(4) 0.65811(15) 0.0555(7) Uani 1 1 d . . . . .
H5A H 0.652482 0.662077 0.694461 0.067 Uiso 1 1 calc R U . . .
H5B H 0.655958 0.414678 0.674933 0.067 Uiso 1 1 calc R U . . .
C6 C 0.84408(18) 0.7503(4) 0.61450(15) 0.0502(6) Uani 1 1 d . . . . .
H6A H 0.921942 0.779689 0.615284 0.060 Uiso 1 1 calc R U . . .
H6B H 0.801413 0.876583 0.627242 0.060 Uiso 1 1 calc R U . . .
C7 C 0.60967(16) 0.7820(4) 0.52365(15) 0.0397(5) Uani 1 1 d . . . . .
C8 C 0.83506(16) 0.6608(4) 0.42826(15) 0.0390(5) Uani 1 1 d . . . . .
C9 C 0.87380(18) 0.8574(4) 0.40019(16) 0.0500(6) Uani 1 1 d . . . . .
H9 H 0.879413 0.966323 0.444515 0.060 Uiso 1 1 calc R U . . .
C10 C 0.90433(19) 0.8944(4) 0.30712(18) 0.0589(7) Uani 1 1 d . . . . .
H10 H 0.930266 1.026588 0.288767 0.071 Uiso 1 1 calc R U . . .
C11 C 0.89553(19) 0.7336(5) 0.24357(17) 0.0559(7) Uani 1 1 d . . . . .
C12 C 0.85925(19) 0.5364(5) 0.26737(17) 0.0600(7) Uani 1 1 d . . . . .
H12 H 0.855090 0.428454 0.222455 0.072 Uiso 1 1 calc R U . . .
C13 C 0.82869(18) 0.5015(4) 0.36066(16) 0.0516(6) Uani 1 1 d . . . . .
H13 H 0.803379 0.368260 0.378134 0.062 Uiso 1 1 calc R U . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0795(11) 0.1259(15) 0.0552(10) 0.0159(9) 0.0221(8) 0.0150(10)
O1 0.0522(11) 0.0474(11) 0.0684(11) -0.0098(9) -0.0146(8) 0.0108(8)
O2 0.0552(11) 0.0557(12) 0.0552(10) -0.0042(8) -0.0128(8) 0.0151(8)
C1 0.0387(13) 0.0364(14) 0.0456(13) 0.0032(10) 0.0009(10) -0.0010(11)
C2 0.0341(12) 0.0359(14) 0.0446(13) 0.0014(10) -0.0014(10) 0.0037(10)
C3 0.0518(16) 0.0526(17) 0.0635(16) 0.0087(13) -0.0045(12) 0.0135(13)
C4 0.0561(16) 0.0664(19) 0.0472(15) 0.0087(13) -0.0102(12) 0.0070(13)
C5 0.0588(17) 0.0544(17) 0.0533(15) 0.0118(12) 0.0044(12) 0.0030(13)
C6 0.0442(14) 0.0538(17) 0.0523(14) 0.0006(12) -0.0072(11) -0.0009(12)
C7 0.0319(12) 0.0473(16) 0.0400(13) 0.0029(11) 0.0034(10) -0.0001(11)
C8 0.0284(12) 0.0413(14) 0.0473(14) -0.0012(11) -0.0007(10) 0.0047(10)
C9 0.0496(15) 0.0463(16) 0.0543(16) -0.0028(12) 0.0024(12) 0.0035(12)
C10 0.0560(17) 0.0564(18) 0.0648(18) 0.0098(15) 0.0099(13) 0.0000(14)
C11 0.0413(15) 0.081(2) 0.0455(15) 0.0124(15) 0.0106(11) 0.0111(14)
C12 0.0555(17) 0.071(2) 0.0531(16) -0.0126(14) 0.0038(13) 0.0058(15)
C13 0.0496(16) 0.0498(16) 0.0555(16) -0.0017(13) 0.0032(12) -0.0052(12)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C11 1.365(3) . ?
O1 C7 1.231(2) . ?
O2 H2 0.8200 . ?
O2 C7 1.309(2) . ?
C1 H1 0.9800 . ?
C1 C2 1.560(3) . ?
C1 C5 1.560(3) . ?
C1 C7 1.498(3) . ?
C2 C3 1.555(3) . ?
C2 C6 1.553(3) . ?
C2 C8 1.495(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.550(3) . ?
C4 H4 0.9800 . ?
C4 C5 1.516(3) . ?
C4 C6 1.540(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C8 C9 1.387(3) . ?
C8 C13 1.385(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.388(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.355(3) . ?
C11 C12 1.364(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.389(3) . ?
C13 H13 0.9300 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O2 H2 109.5 . . ?
C2 C1 H1 109.7 . . ?
C2 C1 C5 98.60(16) . . ?
C5 C1 H1 109.7 . . ?
C7 C1 H1 109.7 . . ?
C7 C1 C2 115.12(17) . . ?
C7 C1 C5 113.65(18) . . ?
C3 C2 C1 99.43(17) . . ?
C6 C2 C1 102.22(16) . . ?
C6 C2 C3 85.74(16) . . ?
C8 C2 C1 117.79(16) . . ?
C8 C2 C3 121.83(18) . . ?
C8 C2 C6 123.34(18) . . ?
C2 C3 H3A 114.8 . . ?
C2 C3 H3B 114.8 . . ?
H3A C3 H3B 111.9 . . ?
C4 C3 C2 82.78(17) . . ?
C4 C3 H3A 114.8 . . ?
C4 C3 H3B 114.8 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 101.59(19) . . ?
C5 C4 H4 120.0 . . ?
C5 C4 C6 102.51(18) . . ?
C6 C4 C3 86.37(17) . . ?
C6 C4 H4 120.0 . . ?
C1 C5 H5A 111.8 . . ?
C1 C5 H5B 111.8 . . ?
C4 C5 C1 99.84(17) . . ?
C4 C5 H5A 111.8 . . ?
C4 C5 H5B 111.8 . . ?
H5A C5 H5B 109.5 . . ?
C2 C6 H6A 114.8 . . ?
C2 C6 H6B 114.8 . . ?
C4 C6 C2 83.20(17) . . ?
C4 C6 H6A 114.8 . . ?
C4 C6 H6B 114.8 . . ?
H6A C6 H6B 111.8 . . ?
O1 C7 O2 122.1(2) . . ?
O1 C7 C1 123.8(2) . . ?
O2 C7 C1 114.1(2) . . ?
C9 C8 C2 122.0(2) . . ?
C13 C8 C2 120.1(2) . . ?
C13 C8 C9 117.9(2) . . ?
C8 C9 H9 119.4 . . ?
C8 C9 C10 121.2(2) . . ?
C10 C9 H9 119.4 . . ?
C9 C10 H10 120.7 . . ?
C11 C10 C9 118.5(2) . . ?
C11 C10 H10 120.7 . . ?
C10 C11 F1 119.2(3) . . ?
C10 C11 C12 122.9(2) . . ?
C12 C11 F1 117.9(3) . . ?
C11 C12 H12 121.0 . . ?
C11 C12 C13 118.0(2) . . ?
C13 C12 H12 121.0 . . ?
C8 C13 C12 121.5(2) . . ?
C8 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C11 C12 C13 -177.75(19) . . . . ?
C1 C2 C3 C4 -67.58(17) . . . . ?
C1 C2 C6 C4 64.38(17) . . . . ?
C1 C2 C8 C9 107.9(2) . . . . ?
C1 C2 C8 C13 -73.3(3) . . . . ?
C2 C1 C5 C4 -1.9(2) . . . . ?
C2 C1 C7 O1 -70.0(3) . . . . ?
C2 C1 C7 O2 110.4(2) . . . . ?
C2 C3 C4 C5 67.61(19) . . . . ?
C2 C3 C4 C6 -34.43(16) . . . . ?
C2 C8 C9 C10 179.4(2) . . . . ?
C2 C8 C13 C12 -179.23(19) . . . . ?
C3 C2 C6 C4 -34.36(16) . . . . ?
C3 C2 C8 C9 -129.0(2) . . . . ?
C3 C2 C8 C13 49.7(3) . . . . ?
C3 C4 C5 C1 -43.1(2) . . . . ?
C3 C4 C6 C2 34.45(16) . . . . ?
C5 C1 C2 C3 46.11(19) . . . . ?
C5 C1 C2 C6 -41.5(2) . . . . ?
C5 C1 C2 C8 179.89(19) . . . . ?
C5 C1 C7 O1 42.7(3) . . . . ?
C5 C1 C7 O2 -137.0(2) . . . . ?
C5 C4 C6 C2 -66.62(18) . . . . ?
C6 C2 C3 C4 34.13(16) . . . . ?
C6 C2 C8 C9 -21.4(3) . . . . ?
C6 C2 C8 C13 157.4(2) . . . . ?
C6 C4 C5 C1 45.7(2) . . . . ?
C7 C1 C2 C3 167.37(18) . . . . ?
C7 C1 C2 C6 79.7(2) . . . . ?
C7 C1 C2 C8 -58.8(3) . . . . ?
C7 C1 C5 C4 -124.3(2) . . . . ?
C8 C2 C3 C4 161.2(2) . . . . ?
C8 C2 C6 C4 -160.1(2) . . . . ?
C8 C9 C10 C11 0.0(3) . . . . ?
C9 C8 C13 C12 -0.4(3) . . . . ?
C9 C10 C11 F1 177.9(2) . . . . ?
C9 C10 C11 C12 -0.8(4) . . . . ?
C10 C11 C12 C13 1.0(4) . . . . ?
C11 C12 C13 C8 -0.3(3) . . . . ?
C13 C8 C9 C10 0.6(3) . . . . ?
_shelx_res_file
;
TITL v75_a.res in P2(1)/n
v75.res
created by SHELXL-2016/6 at 14:06:24 on 12-Dec-2022
REM Old TITL v75 in P2(1)/n
REM SHELXT solution in P2(1)/n
REM R1 0.196, Rweak 0.032, Alpha 0.042, Orientation as input
REM Formula found by SHELXT: C13 O3
CELL 0.71073 12.23 6.3052 14.0798 90 90.886 90
ZERR 4 0.0009 0.0005 0.001 0 0.005 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H F O
UNIT 52 52 4 8
L.S. 4 0 0
PLAN 5
SIZE 0.15 0.12 0.05
TEMP 23
CONF
BOND $H
list 4
MORE -1
fmap 2 53
acta
OMIT -2 50
REM
REM
REM
WGHT 0.034700 0.283500
FVAR 0.70824
F1 3 0.921872 0.769543 0.151103 11.00000 0.07953 0.12588 =
0.05520 0.01585 0.02205 0.01497
O1 4 0.613472 0.951863 0.566723 11.00000 0.05220 0.04744 =
0.06845 -0.00975 -0.01456 0.01082
O2 4 0.543453 0.751325 0.450978 11.00000 0.05524 0.05575 =
0.05524 -0.00421 -0.01281 0.01511
AFIX 147
H2 2 0.502562 0.853674 0.444966 11.00000 -1.50000
AFIX 0
C1 1 0.678533 0.593285 0.549107 11.00000 0.03870 0.03641 =
0.04563 0.00322 0.00092 -0.00101
AFIX 13
H1 2 0.649666 0.467096 0.516740 11.00000 -1.20000
AFIX 0
C2 1 0.802830 0.617148 0.528365 11.00000 0.03415 0.03592 =
0.04463 0.00135 -0.00139 0.00368
C3 1 0.847396 0.421910 0.584263 11.00000 0.05177 0.05263 =
0.06348 0.00867 -0.00454 0.01346
AFIX 23
H3A 2 0.807080 0.291364 0.573597 11.00000 -1.20000
H3B 2 0.925734 0.400483 0.580318 11.00000 -1.20000
AFIX 0
C4 1 0.810392 0.552754 0.671274 11.00000 0.05615 0.06645 =
0.04720 0.00866 -0.01018 0.00702
AFIX 13
H4 2 0.843118 0.525714 0.734085 11.00000 -1.20000
AFIX 0
C5 1 0.687150 0.550783 0.658107 11.00000 0.05883 0.05441 =
0.05325 0.01178 0.00444 0.00303
AFIX 23
H5A 2 0.652482 0.662077 0.694461 11.00000 -1.20000
H5B 2 0.655958 0.414678 0.674933 11.00000 -1.20000
AFIX 0
C6 1 0.844077 0.750340 0.614505 11.00000 0.04418 0.05382 =
0.05228 0.00061 -0.00722 -0.00093
AFIX 23
H6A 2 0.921942 0.779689 0.615284 11.00000 -1.20000
H6B 2 0.801413 0.876583 0.627242 11.00000 -1.20000
AFIX 0
C7 1 0.609672 0.781986 0.523645 11.00000 0.03186 0.04732 =
0.04003 0.00293 0.00336 -0.00010
C8 1 0.835062 0.660790 0.428263 11.00000 0.02842 0.04135 =
0.04733 -0.00124 -0.00067 0.00467
C9 1 0.873795 0.857352 0.400193 11.00000 0.04957 0.04634 =
0.05428 -0.00278 0.00244 0.00348
AFIX 43
H9 2 0.879413 0.966323 0.444515 11.00000 -1.20000
AFIX 0
C10 1 0.904332 0.894370 0.307121 11.00000 0.05597 0.05637 =
0.06478 0.00983 0.00989 0.00004
AFIX 43
H10 2 0.930266 1.026588 0.288767 11.00000 -1.20000
AFIX 0
C11 1 0.895526 0.733569 0.243565 11.00000 0.04126 0.08128 =
0.04547 0.01239 0.01055 0.01108
C12 1 0.859248 0.536409 0.267373 11.00000 0.05548 0.07140 =
0.05311 -0.01256 0.00385 0.00579
AFIX 43
H12 2 0.855090 0.428454 0.222455 11.00000 -1.20000
AFIX 0
C13 1 0.828690 0.501541 0.360663 11.00000 0.04957 0.04984 =
0.05549 -0.00169 0.00325 -0.00519
AFIX 43
H13 2 0.803379 0.368260 0.378134 11.00000 -1.20000
AFIX 0
HKLF 4
REM v75_a.res in P2(1)/n
REM R1 = 0.0479 for 1207 Fo > 4sig(Fo) and 0.0897 for all 1917 data
REM 146 parameters refined using 0 restraints
END
WGHT 0.0347 0.2836
REM Highest difference peak 0.146, deepest hole -0.173, 1-sigma level 0.033
Q1 1 0.7533 0.6533 0.6616 11.00000 0.05 0.15
Q2 1 0.8001 0.7743 0.3985 11.00000 0.05 0.14
Q3 1 0.6224 0.8204 0.4171 11.00000 0.05 0.13
Q4 1 0.5699 0.8437 0.5786 11.00000 0.05 0.13
Q5 1 1.0225 0.9943 0.3341 11.00000 0.05 0.12
;
_shelx_res_checksum 50204
_olex2_submission_special_instructions 'No special instructions were received'